Fused-ring compounds and use thereof as drugs

ABSTRACT

The present invention provides a fused ring compound of the following formula [I] 
                 
 
     wherein each symbol is as defined in the specification, a pharmaceutically acceptable salt thereof, and a therapeutic agent for hepatitis C, which contains this compound. The compound of the present invention shows an anti-hapatitis C virus (HCV) action based on the HCV polymerase inhibitory activity, and is useful as a therapeutic agent or prophylactic agent for hepatitis C.

[0001] This is a continuation in part of PCT/JP00/0918L filed on Dec.22, 2000.

TECHNICAL FIELD

[0002] The present invention relates to a novel fused ring compound anda pharmaceutically acceptable salt thereof useful as a therapeutic agentfor hepatitis C, and to an intermediate compound for the synthesisthereof. The present invention also relates to a novel use of a certainfused ring compound or a pharmaceutically acceptable salt thereof as atherapeutic agent for hepatitis C. More particularly, the presentinvention relates to a therapeutic agent for hepatitis C, which containsa novel fused ring compound or a pharmaceutically acceptable Saltthereof, which is effective for the prophylaxis or treatment ofhepatitis C and which shows anti-hepatitis C virus (HCV) activity,particularly anti-HCV activity based on an RNA-dependent RNA polymeraseinhibitory activity.

BACKGROUND ART

[0003] In 1989, a main causative virus of non-A non-B posttransfusionhepatitis was found and named hepatitis C virus (HCV). Since then,several types of hepatitis viruses have been found besides type A, typeB and type C, wherein hepatitis caused by HCV is called hepatitis C.

[0004] The patients infected with HCV are considered to involve severalpercent of the world population, and the infection with HCVcharacteristically becomes chronic.

[0005] HCV is an envelope RNA virus, wherein the genome is a singlestrand plus-strand RNA, and belongs to the genus Hepacivirus ofFlavivirus (from The International Committee on Taxonomy of Viruses,International Union of Microbiological Societies). Of the same hepatitisviruses, for example, hepatitis B virus (HBV), which is a DNA virus, iseliminated by the immune system and the infection with this virus endsin an acute infection except for neonates and infants having yetimmature immunological competence. In contrast, HCV somehow avoids theimmune system of the host due to an unknown mechanism. Once infectedwith this virus, even an adult having a mature immune system frequentlydevelops persistent infection.

[0006] When chronic hepatitis is associated with the persistentinfection with HCV, it advances to cirrhosis or hepatic cancer in a highrate. Enucleation of tumor by operation does not help much, because thepatient often develops recurrent hepatic cancer due to the sequelainflammation in non-cancerous parts.

[0007] Thus, an effective therapeutic method of hepatitis C is desired.Apart from the symptomatic therapy to suppress; inflammation with ananti-inflammatory agent, the development of a therapeutic agent thatreduces HCV to a low level free from inflammation and that eradicatesHCV has been strongly demanded.

[0008] At present, a treatment with interferon is the only effectivemethod known for the eradication of HCV. However, interferon caneradicate the virus only in about one-third of the patient population.For the rest of the patients, it has no effect or provides only atemporary effect. Therefore, an anti-HCV drug to be used in the place ofor concurrently with interferon is awaited in great expectation.

[0009] In recent years, Ribavirin(1-β-D-ribofuranosyl-1H-1,2,4-triazole-3-carboxamide) has becomecommercially available as a therapeutic agent for hepatitis C, which isto be used concurrently with interferon. It enhances the efficacy ofinterferon but only to a low efficacy rate, and a different noveltherapeutic agent for hepatitis C is desired.

[0010] Also, an attempt has been made to potentiate the immunocompetenceof the patient with an interferon agonist, an interleukin-12 agonist andthe like, thereby to eradicate the virus, but an effectivepharmaceutical agent has not been found yet.

[0011] In addition, the inhibition of HCV growth, wherein HCV-specificprotein is targeted, has been drawing attention these days.

[0012] The gene of HCV encodes a protein such as serine protease, RNAhelicase, RNA-dependent RNA polymerase and the like. These proteinsfunction as a specific protein essential for the growth of HCV.

[0013] One of the specific proteins, RNA-dependent RNA polymerase(hereinafter to be also briefly referred to as an HCV polymerase), is anenzyme essential for the growth of the virus. The gene replication ofHCV having a plus-strand RNA gene is considered to involve synthesis ofa complementary minus-strand RNA by the use of the plus-strand RNA as atemplate, and, using the obtained minus-strand RNA as a template,amplifying the plus-strand RNA. The portion called NS5B of a proteinprecursor, that HCV codes for, has been found to show an RNA-dependentRNA polymerase activity (EMBO J., 15, 12-22, 1996), and is considered toplay a central role in the HCV gene replication.

[0014] Therefore, an HCV polymerase inhibitor can be a target in thedevelopment of an anti-HCV drug, and the development thereof is eagerlyawaited. However, an effective HCV polymerase inhibitor has not beendeveloped yet, like in other attempts to develop an anti-HCV drug basedon other action mechanisms. As the situation stands, no pharmaceuticalagent can treat hepatitis C satisfactorily.

[0015] The following discloses known compounds relatively similar to thecompound of the present invention.

[0016] A known therapeutic agent for hepatitis C having a benzimidazoleskeleton is disclosed in WO97/36866, Japanese Patent Application underPCT laid-open under kohyo No. 2000-511899 (EP906097) and WO99/51619.

[0017] WO97/36866 discloses the following compound D and the like, andHCV helicase inhibitory activity of the compounds.

[0018] Japanese Patent Application under PCT laid-open finder kohyo No.2000-511899 (EP906097) discloses the following compound E and the like,and WO99/51619 discloses the following compound F and the like, in bothof which a possibility of these compounds being effective as an HCVinhibitor is mentioned.

[0019] However, these publications do not include the compound disclosedin the present specification, or a disclosure suggestive thereof.

[0020] A known anti-hepatitis virus agent having a benzimidazoleskeleton is disclosed in Japanese Patent Application under PCT laid-openunder kohyo No. 2000-503017 (WO97/25316) and Japanese Patent Applicationunder PCT laid-open under kohyo No. 0-505092 (WO96/7646) WO97/25316discloses the following compound A and the like, wherein the use thereofis for a treatment of viral infection. The target virus is a DNA virussuch as hepatitis B virus and the like. However, this publication doesnot include the compound disclosed in the present specification or adescription regarding or suggestive of HCV.

[0021] Japanese Patent Application under PCT laid-open under kohyo No.10-505092 discloses the following compound B and the like, wherein theuse thereof is for a treatment of viral infection. The target virus is aDNA virus such as herpesvirus and hepatitis B virus. However, thispublication does not include the compound disclosed in the presentspecification or a description regarding or suggestive of HCV.

[0022] The benzimidazole derivatives having an antiviral activity havebeen disclosed in JP-A-3-31264, U.S. Pat. Nos. 3,644,382 and 3,778,504.In addition, WO98/37072 discloses, as a production inhibitor of tumornecrosis factor (TNF) and cyclic AMP, a benzimidazole derivative for theuse as an anti-human immunodeficiency virus (HIV) agent and ananti-inflammation agent. WO98/05327 discloses, as a reversetranscriptase inhibitor, a benzimidazole derivative for the use as ananti-HIV agent. J. Med. Chem. (13(4), 697-704, 1970) discloses, as aneuraminidase inhibitor, a benzimidazole derivative for the use as ananti-influenza virus agent.

[0023] However, none of these publications includes the compound of thepresent invention or a description regarding or suggestive of ananti-HCV effect.

[0024] Known benzimidazole derivatives having a pharmaceutical use otherthan as an antiviral agent are disclosed in JP-A-8-501318 (U.S. Pat. No.5824651) and JP-A-8-134073 (U.S. Pat. No. 5,563,243). These publicationsdisclose the following compound C and the like as a catechol diethercompound, and the use thereof as an anti-inflammation agent. However,neither of the publications includes the compound of the presentinvention, and as the action mechanism, the former disclosesphosphodiesterase IV and the latter discloses TNF. These publications donot include a description regarding or suggestive of an anti-HCV effect.

[0025] Japanese Patent Application under PCT laid-open under kohyo No.2000-159749 (EP882718) discloses the following compound G and the like,and the use thereof for the treatment of bronchitis, glomerulonephritisand the like. However, this publication does not include the compound ofthe present invention, but discloses only a phosphodiesterase IVinhibitory and hypoglycemic action. This publication does not include adescription regarding or suggestive of an anti-HCV effect.

[0026] U.S. Pat. No. 6,211,177 discloses the following compound H andthe like with their use as antitumor agents. However, this publicationdoes not encompass the compound of the present invention, and does notdisclose or suggest an anti-HCV effect.

[0027] WO98/50029, WO98/50030 and WO98/50031 disclose benzimidazolederivatives as an antitumor agent having a protein isoprenyl transferaseaction. While this publication discloses a wide scope of the claims, atleast it does not include a compound analogous to the compound of thepresent invention or a description regarding or suggestive of ananti-HCV effect.

[0028] JP-A-8-109169 (EP694535) discloses the application of atachykinin receptor antagonist to treat an inflammatory disease, andWO96/35713 discloses the application thereof as a growth hormone releasepromoter to treat a growth hormone-related disease such as osteoporosisand the like. However, none of these publications includes a descriptionregarding or suggestive of an anti-HCV effect.

[0029] WO2001/21634 discloses the following compound I in a chemicallibrary. However, this publication does not encompass the compound ofthe present invention. While it discloses an antimicrobial activity ofcertain compounds, this publication does not teach or suggest ananti-HCV effect.

[0030] JP-A-53-14735 discloses a benzimidazole derivative as abrightener besides its pharmaceutical use, but this publication does notinclude the compound of the present invention.

SUMMARY OF THE INVENTION

[0031] Based on the findings from the preceding studies, it has beenelucidated that a pharmaceutical agent having an anti-HCV activity iseffective for the prophylaxis and treatment of hepatitis C, andparticularly an anti-HCV agent having fin inhibitory activity onRNA-dependent RNA polymerase of HCV can be a prophylactic andtherapeutic agent effective against hepatitis C and a prophylactic andtherapeutic agent for the disease caused by hepatitis C.

[0032] Accordingly, the present invention provides a pharmaceuticalagent having an anti-HCV activity, particularly a pharmaceutical agenthaving an RNA-dependent RNA polymerase inhibitory activity.

[0033] The present inventors have made an in-depth study of compoundshaving an anti-HCV activity, particularly RNA-dependent RNA polymeraseinhibitory activity, and completed the present invention.

[0034] Thus, the present invention provides the following (1) to (117).

[0035] (1) A therapeutic agent for hepatitis C, which comprises a fusedring compound of the following formula [I] or a pharmaceuticallyacceptable salt thereof as an active ingredient:

[0036] wherein

[0037] a broken line is a single bond or a double bond,

[0038] G¹ is C(—R¹) or a nitrogen atom,

[0039] G² is C(—R²) or a nitrogen atom,

[0040] G³ is C(—R³) or a nitrogen atom,

[0041] G⁴ is C(—R⁴) or a nitrogen atom,

[0042] G⁵, G⁶, G⁸ and G⁹ are each independently a carbon atom or anitrogen atom,

[0043] G⁷ is C(—R⁷), an oxygen atom, a sulfur atom, or a nitrogen atomoptionally substituted by R⁸,

[0044] wherein R¹, R², R³ and R⁴ are each independently,

[0045] (1) hydrogen atom,

[0046] (2) C₁₋₆ alkanoyl,

[0047] (3) carboxyl,

[0048] (4) cyano,

[0049] (5) nitro,

[0050] (6) C₁₋₆ alkyl optionally substituted by 1 to 3 substituent(s)selected from the following group A,

[0051] group A; halogen atom, hydroxyl group, carboxyl, amino, C₁₋₆alkoxy, C₁₋₆ alkoxy C₁₋₆ alkoxy, C₁₋₆ alkoxycarbonyl and C₁₋₆alkylamino,

[0052] (7) —COOR^(a1)

[0053] wherein R^(a1) is optionally substituted C₁₋₆ alkyl (as definedabove), C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the following group B or glucuronic acidresidue,

[0054] group B; halogen atom, cyano, nitro, C₁₋₆ alkyl, halogenated C₁₋₆alkyl, C₁₋₆ alkanoyl, —(CH₂)_(r)—COOR^(b1), —(CH₂)_(r)—CONR^(b1)R^(b2),(CH₂)_(r)—NR^(b1)R^(b2), —(CH₂)_(r)—NR^(b1)—COR^(b2),—(CH₂)_(r)—NHSO₂R^(b1), —(CH₂)_(r)—OR^(b1), —(CH₂)_(r)—SR^(b1),—(CH₂)_(r)—SO₂R^(b1) and —(CH₂)_(r)—SO₂NR^(b1)R^(b2) wherein R^(b1) andR^(b2) are each independently hydrogen atom or C₁₋₆ alkyl and r is 0 oran integer of 1 to 6,

[0055] (8) —CONR^(a2)R^(a1)

[0056] wherein R^(a2) and R^(a3) are each independently hydrogen atom,C₁₋₆ alkoxy or optionally substituted C₁₋₆ alkyl (as defined above),

[0057] (9) —C (═NR^(a4) )NH₂

[0058] wherein R^(a4) is hydrogen atom or hydroxyl group,

[0059] (10) —NHR^(a5)

[0060] wherein R^(a5) is hydrogen atom, C₁₋₆ alkanoyl or C₁₋₆alkylsulfonyl,

[0061] (11) —OR^(a6)

[0062] wherein R^(a6) is hydrogen atom or optionally substituted C₁₋₆alkyl (as defined above),

[0063] (12) —SO₂R^(a7)

[0064] wherein R^(a7) is hydroxyl group, amino, C₁₋₆ alkyl or C₁₋₆alkylamino,

[0065] (13) —P(═O) (OR^(a31))₂

[0066] wherein R^(a31) is hydrogen atom, optionally substituted C₁₋₆alkyl (as defined above) or C₆₋₁₄ aryl C₁₋₆ alkyl optionally substitutedby 1 to 5 substituent(s) selected from the above group B

[0067] or

[0068] (14) heterocyclic group having 1 to 4 heteroatom(s) selected froman oxygen atom, a nitrogen atom and a sulfur atom, and

[0069] R⁷ and R⁸ are each hydrogen atom or optionally substituted C₁₋₆alkyl (as defined above),

[0070] ring Cy is

[0071] (1) C₃₋₈ cycloalkyl optionally substituted by 1 to 5substituent(s) selected from the following group C, group C; hydroxylgroup, halogen atom, C₁₋₆ alkyl and C₁₋₆ alkoxy,

[0072] (2) C₃₋₈ cycloalkenyl optionally substituted by 1 to 5substituent(s) selected from the above group C, or

[0073] wherein u and v are each independently an integer of 1 to 3,

[0074] ring A is

[0075] (1) C₆₋₁₄ aryl,

[0076] (2) C₃₋₈ cycloalkyl,

[0077] (3) C₃₋₈ cycloalkenyl or

[0078] (4) heterocyclic group having 1 to 4 heteroatom(s) selected froman oxygen atom, a nitrogen atom and a sulfur atom,

[0079] R⁵ and R⁶ are each independently

[0080] (1) hydrogen atom,

[0081] (2) halogen atom,

[0082] (3) optionally substituted C₁₋₆ alkyl (as defined above)

[0083] or

[0084] (4) —OR^(a8)

[0085] wherein R^(a8) is hydrogen atom, C₁₋₆ alkyl or C₆₋₁₄ aryl C₁₋₆alkyl, and

[0086] X is

[0087] (1) hydrogen atom,

[0088] (2) halogen atom,

[0089] (3) cyano,

[0090] (4) nitro,

[0091] (5) amino, C₁₋₆ alkanoylamino,

[0092] (6) C₁₋₆ alkylsulfonyl,

[0093] (7) optionally substituted C₁₋₆ alkyl (as defined above),

[0094] (8) C₂₋₆ alkenyl optionally substituted by 1 to 3 substituent(s)selected from the above group A,

[0095] (9) —COOR^(a9)

[0096] wherein R^(a9) is hydrogen atom or C₁₋₆ alkyl,

[0097] (10) —CONH—(CH₂)₁—R^(a10)

[0098] wherein R^(a10) is optionally substituted C₁₋₆ alkyl (as definedabove), C₁₋₆ alkoxycarbonyl or C₁₋₆ alkanoylamino and 1 is 0 or aninteger of 1 to 6,

[0099] (11) —OR^(a11)

[0100] wherein R^(a11) is hydrogen atom or optionally substituted C₁₋₆alkyl (as defined above)

[0101] or

[0102] wherein

[0103] ring B is

[0104] (1′) C₆₋₁₄ aryl,

[0105] (2′) C₃₋₈ cycloalkyl or

[0106] (3′) heterocyclic group (as defined above),

[0107] each Z is independently

[0108] (1′) a group selected from the following group D,

[0109] (2′) C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the following group D,

[0110] (3′) C₃₋₈ cycloalkyl optionally substituted by 1 to 5substituent(s) selected from the following group D,

[0111] (4′) C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the following group D,

[0112] (5′) heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the following group D,

[0113]  wherein the heterocyclic group has 1 to 4 heteroatom(s) selectedfrom an oxygen atom, a nitrogen atom and a sulfur atom, or

[0114] (6′) heterocycle C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the following group D,

[0115]  wherein the heterocycle C₁₋₆ alkyl is C₁₋₆ alkyl substituted byheterocyclic group optionally substituted by 1 to 5 substituent(s)selected from the group D, as defined above,

[0116] group D:

[0117] (a) hydrogen atom,

[0118] (b) halogen atom,

[0119] (c) cyano,

[0120] (d) nitro,

[0121] (e) optionally substituted C₁₋₆ alkyl (as defined above),

[0122] (f) —(CH₂)_(t)—COR^(a18),

[0123] (hereinafter each t means independently 0 or an integer of 1 to6),

[0124] wherein R^(a18) is

[0125] (1″) optionally substituted C₁₋₆ alkyl (as defined above),

[0126] (2″) C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the above group B or

[0127] (3″) heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B wherein the heterocyclicgroup has 1 to 4 heteroatom(s) selected from an oxygen atom, a nitrogenatom and a sulfur atom,

[0128] (g) —(CH₂)_(t)—COOR^(a19)

[0129] wherein R^(a19) is hydrogen atom, optionally substituted C₁₋₆alkyl (as defined above) or C₆₋₁₄ aryl C₁₋₆ alkyl optionally substitutedby 1 to 5 substituent(s) selected from the above group B,

[0130] (h) —(CH₂)_(t)—CONR^(a27)R^(a28)

[0131] wherein R^(a27) and R^(a28) are each independently,

[0132] (1″) hydrogen atom,

[0133] (2″) optionally substituted C₁₋₆ alkyl (as defined above),

[0134] (3″) C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the above group B,

[0135] (4″) C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0136] (5″) heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0137] (6″) heterocycle C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0138]  wherein the heterocycle C₁₋₆ alkyl is C₁₋₆ alkyl substituted byheterocyclic group optionally substituted by 1 to 5 substituent(s)selected from the above group B, as defined above,

[0139] (7″) C₃₋₈ cycloalkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0140] (8″) C₃₋₈ cycloalkyl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0141] (9″) hydroxyl group or

[0142] (10″) C₁₋₆ alkoxy,

[0143] (i) —(CH₂)_(t)—C (═NR^(a33))NH₂

[0144] wherein R^(a33) is hydrogen atom, C₁₋₆ alkyl, hydroxyl group orC₁₋₆ alkoxy, p3 (j) —(CH₂)_(t)—OR^(a20)

[0145] wherein R^(a20) is

[0146] (1″) hydrogen atom,

[0147] (2″) optionally substituted C₁₋₆ alkyl (as defined above),

[0148] (3″) optionally substituted C₂₋₆ alkenyl (as defined above),

[0149] (4″) C₂₋₆ alkynyl optionally substituted by 1 to 3 substituent(s)selected from the above group A,

[0150] (5″) C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the above group B,

[0151] (6″) C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0152] (7″) heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0153] (8″) heterocycle C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0154] (9″) C₃₋₈ cycloalkyl optionally substituted by 1 to 5substituent(s) selected from the above group B, or

[0155] (10″) C₃₋₈ cycloalkyl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0156] (k) —(CH₂)_(t)—O—(CH₂)_(p)—COR^(a21)

[0157] wherein R^(a21) is amino, C₁₋₆ alkylamino or heterocyclic groupoptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B,

[0158] and p is 0 or an integer of 1 to 6,

[0159] (l) —(CH₂)_(t)—NR^(a22)R^(a23)

[0160] wherein R^(a22) and R^(a23) are each independently

[0161] (1″) hydrogen atom,

[0162] (2″) optionally substituted C₁₋₆ alkyl (as defined above),

[0163] (3″) C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the above group B,

[0164] (4″) C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0165] (5″) heterocycle C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B or

[0166] (6″) heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0167] (m) —(CH₂)_(t)—NR^(a29)CO—R^(a24)

[0168] wherein R^(a29) is hydrogen atom, C₁₋₆ alkyl or C₁₋₆ alkanoyl,and

[0169] R^(a24) is

[0170] (1″) amino,

[0171] (2″) C₁₋₆ alkylamino,

[0172] (3″) optionally substituted C₁₋₆ alkyl (as defined above),

[0173] (4″) C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the above group B,

[0174] (5″) heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B or

[0175] (6″) heterocycle C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0176] (n) —(CH₂)_(t)—NR^(a29)SO₂—R^(a25)

[0177] wherein R^(a29) is as defined above, and R^(a25) is hydrogenatom, optionally substituted C₁₋₆ alkyl (as defined above), C₆₋₁₄ aryloptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B or heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0178] (o) —(CH₂)_(t)—S(O)_(q)—R^(a25)

[0179] wherein R^(a25) is as defined above, and q is 0, 1 or 2,

[0180] (p) —(CH₂)_(t)—SO₂—NHR^(a26)

[0181] wherein R^(a26) is hydrogen atom, optionally substituted C₁₋₆alkyl (as defined above), C₆₋₁₄ aryl optionally substituted by 1 to 5substituent(s) selected from the above group B or heterocyclic groupoptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B,

[0182] and

[0183] (q) heterocyclic group having 1 to 4 heteroatom(s) selected froman oxygen atom, a nitrogen atom and a sulfur atom, and

[0184] w is an integer of 1 to 3, and

[0185] Y is

[0186] (1′) a single bond,

[0187] (2′) C₁₋₆ alkylene,

[0188] (3′) C₂₋₆ alkenylene,

[0189] (4′) —(CH₂)_(m)—O—(CH₂)_(n)—,

[0190] (hereinafter m and n are each independently 0 or an integer of 1to 6),

[0191] (5′) —CO—,

[0192] (6′) —CO₂—(CH₂)_(n)—,

[0193] (7′) —CONH—(CH₂)_(n)—NH—,

[0194] (8′) —NHCO₂—,

[0195] (9′) —NHCONH—,

[0196] (10′) —O—(CH₂)_(n)—CO—,

[0197] (11′) —O—(CH₂)_(n)—O—,

[0198] (12′) —SO₂—,

[0199] (13′) —(CH₂)_(m)—NR^(a12)—(CH₂)_(n)—

[0200] wherein R^(a12) is

[0201] (1″) hydrogen atom,

[0202] (2″) optionally substituted C₁₋₆ alkyl (as defined above),

[0203] (3″) C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0204] (4″) C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the above group B,

[0205] (5″) —COR^(b5)

[0206]  wherein R^(b5) is hydrogen atom, optionally substituted C₁₋₆alkyl (as defined above), C₆₋₁₄ aryl optionally substituted by 1 to 5substituent(s) selected from the above group B or C₆₋₁₄ aryl C₁₋₆ alkyloptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B,

[0207] (6″) —COOR^(b5) (R^(b5) is as defined above) or

[0208] (7″) —SO₂R^(b5) (R^(b5) is as defined above),

[0209] (14′) —NR^(a12)CO— (R^(a12) is as defined above),

[0210] (15′) —CONR^(a13)—(CH₂)_(n)—

[0211] wherein R^(a13) is hydrogen atom, optionally substituted C₁₋₆alkyl (as defined above) or C₆₋₁₄ aryl C₁₋₆ alkyl optionally substitutedby 1 to 5 substituent(s) selected from the above group B,

[0212] (16′) —CONH—CHR^(a14)—

[0213] wherein R^(a14) is C₆₋₁₄ aryl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0214] (17′) —O—(CH₂)_(m)—CR^(a15)R^(a16)—(CH₂)_(n)—

[0215] wherein R^(a15) and R^(a16) are each independently

[0216] (1″) hydrogen atom,

[0217] (2″) carboxyl,

[0218] (3″) C₁₋₆ alkyl,

[0219] (4″) —OR^(b6)

[0220] wherein R^(b6) is C₁₋₆ alkyl or C₆₋₁₄ aryl C₁₋₆ alkyl, or

[0221] (5″) —NHR^(b7)

[0222] wherein R^(b7) is hydrogen atom, C₁₋₆ alkyl, C₁₋₆ alkanoyl orC₆₋₁₄ aryl C₁₋₆ alkyloxycarbonyl, or R^(a15) is optionally

[0223] wherein n′, ring B′, Z′ and w′ are the same as theabove-mentioned n, ring B, Z and w, respectively, and may be the same asor different from the respective counterparts,

[0224] (18′) —(CH₂)_(n)—NR^(a12)—CHR^(a15)— (R^(a12) and R^(a15) areeach as defined above),

[0225] (19′) —NR^(a17)SO₂—

[0226] wherein R^(a17) is hydrogen atom or C₁₋₆ alkyl,

[0227] (20′) —S(O)_(e)—(CH₂)_(m)—CR^(a15)R^(a16)—(CH₂)_(n)— (e is 0, 1or 2, R^(a15) and R^(a16) are each as defined above),

[0228] or

[0229] (21′) —(CH₂)_(m)—CR^(a15)R^(a16)—(CH₂)_(n)— (R^(a15) and R^(a16)are each as defined above).

[0230] (2) The therapeutic agent of (1) above, wherein 1 to 4 of the G¹,G², G³, G⁴, G⁵, G⁶, G⁷, G³ and G⁹ is (are) a nitrogen atom.

[0231] (3) The therapeutic agent of (2) above, wherein G² is C(—R²) andG⁶ is a carbon atom.

[0232] (4) The therapeutic agent of (2) or (3) above, wherein G⁵ is anitrogen atom.

[0233] (5) The therapeutic agent of (1) above, wherein, in formula [I],the moiety

[0234] is a fused ring selected from

[0235] (6) The therapeutic agent of (5) above, wherein, in formula [I],the moiety

[0236] is a fused ring selected from

[0237] (7) The therapeutic agent of (6) above, which comprises a fusedring compound of the following formula [I-1]

[0238] wherein each symbol is as defined in (1),

[0239] or a pharmaceutically acceptable salt thereof as an activeingredient.

[0240] (8) The therapeutic agent of (6) above, which comprises a fusedring compound of the following formula [I-2]

[0241] wherein each symbol is as defined in (1),

[0242] or a pharmaceutically acceptable salt thereof as an activeingredient.

[0243] (9) The therapeutic agent of (6) above, which comprises a fusedring compound of the following formula [I-3]

[0244] wherein each symbol is as defined in (1),

[0245] or a pharmaceutically acceptable salt thereof as an activeingredient.

[0246] (10) The therapeutic agent of (6) above, which comprises a fusedring compound of the following formula [I-4]

[0247] wherein each symbol is as defined in (1),

[0248] or a pharmaceutically acceptable salt thereof as an activeingredient.

[0249] (11) The therapeutic agent of any of (1) to (10) above, whereinat least one of R¹, R², R³ and R⁴ is carboxyl, —COOR^(a1),—CONR^(a2)R^(a3), —SO₂R^(a7) (wherein R^(a1), R^(a2), R^(a3) and R^(a7)are as defined in (1)),

[0250] (12) The therapeutic agent of (11) above, wherein at least one ofR¹, R², R³ and R⁴ is carboxyl, —COOR^(a1), —CONR^(a2)R^(a3) or—SO₂R^(a7) wherein R^(a1), R^(a2), R^(a3) and R^(a7) are as defined in(1).

[0251] (13) The therapeutic agent of any of (1) to (10) above, whereinat least one of R¹, R², R³ and R⁴ is —COOR^(a1) wherein R^(a1) isglucuronic acid residue.

[0252] (14) The therapeutic agent of any of (1) to (10) above, whereinat least one of R¹, R², R³ and R⁴ is heterocyclic group having 1 to 4heteroatom(s) selected from an oxygen atom, a nitrogen atom and a sulfuratom.

[0253] (15) The therapeutic agent of any of (1) to (14) above, whereinthe ring Cy is cyclopentyl, cyclohexyl, cycloheptyl,tetrahydrothiopyranyl or piperidino.

[0254] (16) The therapeutic agent of any of (1) to (14) above, whereinthe ring Cy is

[0255] wherein each symbol is as defined in (1).

[0256] (17) The therapeutic agent of any of (1) to (16) above, whereinthe ring A is C₆₋₁₄ aryl.

[0257] (18) The therapeutic agent of any of (1) to (17) above, whereinat least one substituent optionally substituted by group A is asubstituent substituted by C₁₋₆ alkoxy C₁₋₆ alkoxy.

[0258] (19) The therapeutic agent of any of (1) to (17) above, whereinthe Y is —(CH₂)_(m)—CR^(a15)R^(a16)—(CH₂)_(n)— wherein each symbol is asdefined in (1).

[0259] (20) The therapeutic agent of any of (1) to (19) above, whereinat least one group represented by Z is heterocycle C₁₋₆ alkyl optionallysubstituted by 1 to 5 substituent(s) selected from the group D.

[0260] (21) The therapeutic agent of any of (1) to (19) above, whereinat least one group represented by Z is a heterocyclic group optionallysubstituted by 1 to 5 substituent(s) selected from the group D, whereinsaid heterocyclic group is selected from the following groups:

[0261] wherein E¹ is an oxygen atom, a sulfur atom or N(—R^(a35)) E² isan oxygen atom, CH₂ or N(—R^(a35)), E³ is an oxygen atom or a sulfuratom, wherein each R^(a35) is independently hydrogen atom or C_(1-E)alkyl, f is an integer of 1 to 3, and h and h′ are the same or differentand each is an integer of 1 to 3.

[0262] (22) The therapeutic agent of (21) above, wherein at least onegroup represented by Z is heterocyclic group optionally substituted by 1to 5 substituent(s) selected from the group D wherein said heterocyclicgroup is selected from the following groups:

[0263] wherein each symbol is as defined in (21).

[0264] (23) The therapeutic agent of any of (1) to (19) above, whereinat least one group represented by group D is—(CH₂)_(t)—CONR^(a27)R^(a28) wherein each symbol is as defined in (1),and at least one of R^(a27) and R^(a28) is C₁₋₆ alkoxy.

[0265] (24) The therapeutic agent of any of (1) to (19) above, whereinat least one group represented by group D is —(CH₂)_(t)—C(═NR^(a33) )NH₂wherein each symbol is as defined in (1), and R^(a33) is hydroxyl groupor C₁₋₆ alkoxy.

[0266] (25) The therapeutic agent of any of (1) to (19) above, whereinat least one group represented by group D is—(CH₂)_(t)—O—(CH₂)_(p)—COR^(a21) wherein each symbol is as defined in(1), and R^(a21) is amino.

[0267] (26) The therapeutic agent of any of (1) to (19) above, whereinat least one group represented by group D is—(CH₂)_(t)—NR^(a29)CO—R^(a24) wherein each symbol is as defined in (1),and R^(a24) is amino or C₁₋₆ alkylamino.

[0268] (27) The therapeutic agent of any of (1) to (19) above, whereinat least one group represented by group D is —(CH₂)_(t)—NR^(a22)R^(a23)wherein each symbol is as defined in (1), and at lease one of R^(a22)and R^(a23) is heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the group B.

[0269] (28) The therapeutic agent of any of (1) to (19) above, whereinat least one group represented by group D is heterocyclic group having 1to 4 heteroatom(s) selected from an oxygen atom, a nitrogen atom and asulfur atom.

[0270] (29) The therapeutic agent of (1) above, which comprises a fusedring compound of the following formula [I] or a pharmaceuticallyacceptable salt thereof as an active ingredient:

[0271] wherein

[0272] a broken line is a single bond or a double bond,

[0273] G¹ is C(—R¹) or a nitrogen atom,

[0274] G² is C(—R²) or a nitrogen atom,

[0275] G³ is C(—R³) or a nitrogen atom,

[0276] G⁴ is C(—R⁴) or a nitrogen atom,

[0277] G⁵, G⁶, G⁸ and G⁹ are each independently a carbon atom or anitrogen atom,

[0278] G⁷ is C(—R⁷), an oxygen atom, a sulfur atom, or a nitrogen atomoptionally substituted by R⁸,

[0279] wherein R¹, R², R³ and R⁴ are each independently,

[0280] (1) hydrogen atom,

[0281] (2) C₁₋₆ alkanoyl,

[0282] (3) carboxyl,

[0283] (4) cyano,

[0284] (5) nitro,

[0285] (6) C₁₋₆ alkyl optionally substituted by 1 to 3substituent(s)selected from the following group A,

[0286] group A; halogen atom, hydroxyl group, carboxyl, amino, C₁₋₆alkoxy, C₁₋₆ alkoxycarbonyl and (C₁₋₆ alkylamino,

[0287] (7) —COOR^(a1)

[0288] wherein R^(a1) is optionally substituted C₁₋₆ alkyl (as definedabove) or C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the following group B,

[0289] group B; halogen atom, cyano, nitro, C₁₋₆ alkyl, halogenated C₁₋₆alkyl, C₁₋₆ alkanoyl, —(CH₂)_(r)—COOR^(b), —(CH₂)_(r)—CONR^(b1)R^(b2),—(CH₂)_(r)—NR^(b1)R^(b2), —(CH₂)_(r)—NR^(b1)—COR^(b2),—(CH₂)_(r)—NHSO₂R^(b1), —(CH₂)_(r)—OR^(b1), —(CH₂)_(r)—SR^(b1),—(CH₂)_(r)—SO₂R^(b1) and —(CH₂)_(r)—SO₂NR^(b1)R^(b2)

[0290] wherein R^(b1) and R^(b2) are each independently hydrogen atom orC₁₋₆ alkyl and r is 0 or an integer of 1 to 6,

[0291] (8) —CONR^(a2)R^(a3)

[0292] wherein R^(a2) and R^(a3) are each independently hydrogen atom,C₁₋₆ alkoxy or optionally substituted C₁₋₆ alkyl (as defined above),

[0293] (9) —C (═NR^(a4))NH₂

[0294] wherein R^(a4) is hydrogen atom or hydroxyl group,

[0295] (10 ) —NHR^(a5)

[0296] wherein R^(a5) is hydrogen atom, C₁₋₆ alkanoyl or C₁₋₆alkylsulfonyl,

[0297] (11) —OR^(a6)

[0298] wherein R^(a6) is hydrogen atom or optionally substituted C₁₋₆alkyl(as defined above),

[0299] (12) —SO₂R^(a7)

[0300] wherein R^(a7) is hydroxyl group, amino, C₁₋₆ alkyl or C₁₋₆alkylamino

[0301] or

[0302] (13) —P(═O) (OR^(a31))₂

[0303] wherein R^(a31) is hydrogen atom, optionally substituted C₁₋₆alkyl (as defined above) or C₆₋₁₄ aryl C₁₋₆ alkyl optionally substitutedby 1 to 5 substituent.(s) selected from the above group B, and

[0304] R⁷ and R⁸ are each hydrogen atom or optionally substituted C₁₋₆alkyl(as defined above),

[0305] ring Cy is

[0306] (1) C₃₋₈ cycloalkyl optionally substituted by 1 to 5substituent(s) selected from the following group C, group C; hydroxylgroup, halogen atom, C₁₋₆ alkyl and C₁₋₆ alkoxy,

[0307] (2) C₃₋₈ cycloalkenyl optionally substituted by 1 to 5substituent(s) selected from the above group C, or

[0308] wherein u and v are each independently an integer of 1 to 3,

[0309] ring A is

[0310] (1) C₆₋₁₄ aryl,

[0311] (2) C₃₋₈ cycloalkyl,

[0312] (3) C₃₋₈ cycloalkenyl or

[0313] (4) heterocyclic group having 1 to 4 heteroatom(s) selected froman oxygen atom, a nitrogen atom and a sulfur atom,

[0314] R⁵ and R⁶ are each independently

[0315] (1) hydrogen atom,

[0316] (2) halogen atom,

[0317] (3) optionally substituted C₁₋₆ alkyl (as defined above)

[0318] or

[0319] (4) —OR^(a8)

[0320] wherein R^(a8) is hydrogen atom, C₁₋₆ alkyl or C₆₋₁₄ aryl C₁₋₆alkyl, and

[0321] X is

[0322] (1) hydrogen atom,

[0323] (2) halogen atom,

[0324] (3) cyano,

[0325] (4) nitro,

[0326] (5) amino, C₁₋₆ alkanoylamino,

[0327] (6) C₁₋₆ alkylsulfonyl,

[0328] (7) optionally substituted C₁₋₆ alkyl (as defined above),

[0329] (8) C₂₋₆ alkenyl optionally substituted by 1 to 3 substituent(s)selected from the above group A,

[0330] (9) —COOR^(a9)

[0331] wherein R^(a9) is hydrogen atom or C₁₋₆ alkyl,

[0332] (10) —CONH—(CH₂)_(l)—R^(a10)

[0333] wherein R^(a10) is optionally substituted C₁₋₆ alkyl (as definedabove), C₁₋₆ alkoxycarbonyl or C₁₋₆ alkanoylamino and 1 is 0 or aninteger of 1 to 6,

[0334] (11) —OR^(a11)

[0335] wherein R^(a11) is hydrogen atom or optionally substituted C₁₋₆alkyl (as defined above)

[0336] or

[0337] wherein

[0338] ring B is

[0339] (1′) C₆₋₁₄ aryl,

[0340] (2′) C₃₋₈ cycloalkyl or

[0341] (3′) heterocyclic group (as defined above),

[0342] each Z is independently

[0343] (1′) a group selected from the following group D,

[0344] (2′) C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the following group D,

[0345] (3′) C₃₋₈ cycloalkyl optionally substituted by 1 to 5substituent(s) selected from the following group D,

[0346] (4′) C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the following group D or

[0347] (5′) heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the following group D

[0348]  wherein the heterocyclic group has 1 to 4; heteroatom(s)selected from an oxygen atom, a nitrogen atom and a sulfur atom, groupD:

[0349] (a) hydrogen atom,

[0350] (b) halogen atom,

[0351] (c) cyano,

[0352] (d) nitro,

[0353] (e) optionally substituted C₁₋₆ alkyl (as defined above),

[0354] (f) —(CH₂)_(t)—COR^(a18),

[0355] (hereinafter each t means independently 0 or an integer of 1 to6),

[0356] wherein R^(a18) is

[0357] (1″) optionally substituted C₁₋₆ alkyl (as defined above),

[0358] (2″) C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the above group B or

[0359] (3″) heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B wherein the heterocyclicgroup has 1 to 4 heteroatom(s) selected from an oxygen atom, a nitrogenatom and a sulfur atom,

[0360] (g) —(CH₂)_(t)—COOR^(a19)

[0361] wherein R^(a19) is hydrogen atom, optionally substituted C₁₋₆alkyl (as defined above) or C₆₋₁₄ aryl C₁₋₆ alkyl optionally substitutedby 1 to 5 substituent(s) selected from the above group B,

[0362] (h) —(CH₂)_(t)—CONR^(a27)R^(a28)

[0363] wherein R^(a27) and R^(a28) are each independently,

[0364] (1″) hydrogen atom,

[0365] (2″) optionally substituted C₁₋₆ alkyl (as defined above),

[0366] (3″) C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the above group B,

[0367] (4″) C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0368] (5″) heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0369] (6″) heterocycle C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0370]  wherein the heterocycle C₁₋₆ alkyl is C₁₋₆ alkyl substituted byheterocyclic group optionally substituted by 1 to 5 substituent(s)selected from the above group B, as defined above,

[0371] (7″) C₃₋₈ cycloalkyl optionally substituted by 1 to 5substituent(s) selected from the above group B, or

[0372] (8″) C₃₋₈ cycloalkyl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0373] (i) —(CH₂)_(t)—C(═NR^(a33))NH₂

[0374] wherein R^(a33) is hydrogen atom or C₁₋₆ alkyl,

[0375] (j) —(CH₂)_(t)—OR^(a20)

[0376] wherein R^(a20) is

[0377] (1″) hydrogen atom,

[0378] (2″) optionally substituted C₁₋₆ alkyl (as defined above),

[0379] (3″) optionally substituted C₂₋₆ alkenyl (as defined above),

[0380] (4″) C₂₋₆ alkynyl optionally substituted by 1 to 3 substituent(s)selected from the above group A,

[0381] (5″) C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the above group B,

[0382] (61″) C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0383] (7″) heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0384] (8″) heterocycle C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0385] (9 ″) C₃₋₈ cycloalkyl optionally substituted by 1 to 5substituent(s) selected from the above group B, or

[0386] (10″) C₃₋₈ cycloalkyl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0387] (k) —(CH₂)_(t)—O—(CH₂)_(p)—COR^(a21)

[0388] wherein R^(a21) is C₁₋₆ alkylamino or heterocyclic groupoptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B, and p is 0 or an integer of 1 to 6,

[0389] (l) —(CH₂)_(t)—NR^(a22)R^(a23)

[0390] wherein R^(a22) and R^(a23) are each independently

[0391] (11″) hydrogen atom,

[0392] (211) optionally substituted C₁₋₆ alkyl (as defined above),

[0393] (3″) C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the above group B,

[0394] (4″) C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B or

[0395] (5″) heterocycle C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0396] (m) —(CH₂)_(t)—NR^(a29)CO—R^(a24)

[0397] wherein R^(a29) is hydrogen atom, C₁₋₆ alkyl or C₁₋₆ alkanoyl,R^(a24) is optionally substituted C₁₋₆ alkyl (as defined above), C₆₋₁₄aryl optionally substituted by 1 to 5 substituent(s) selected from theabove group B or heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0398] (n) —(CH₂)_(t)—NHSO₂—R^(a25)

[0399] wherein R^(a25) is hydrogen atom, optionally substituted C₁₋₆alkyl (as defined above), C₆₋₁₄ aryl optionally substituted by 1 to 5substituent(s) selected from the above group B or heterocyclic groupoptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B,

[0400] (o) —(CH₂)_(t)—S(O)_(q)—R^(a25)

[0401] wherein R^(a25) is as defined above, and q is 0, 1 or 2,

[0402] and

[0403] (p) —(CH₂)_(t)—SO₂—NHR^(a26)

[0404] wherein R^(a26) is hydrogen atom, optionally substituted C₁₋₆alkyl (as defined above), C₆₋₁₄ aryl optionally substituted by(1 to 5substituent(s) selected from the above group B or heterocyclic groupoptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B,

[0405] w is an integer of 1 to 3, and

[0406] Y is

[0407] (1′) a single bond,

[0408] (2′) C₁₋₆ alkylene,

[0409] (3′) C₂₋₆ alkenylene,

[0410] (4′) —(CH₂)_(m)—O—(CH₂)_(n)—,

[0411] (hereinafter m and n are each independently 0

[0412] or an integer of 1 to 6),

[0413] (5′) —CO—,

[0414] (6′) —CO₂—(CH₂)_(n)—,

[0415] (7′) —CONH—(CH₂)_(n)—NH—,

[0416] (8′) —NHCO₂—,

[0417] (9′) —NHCONH—,

[0418] (10′) —O—(CH₂)_(n)—CO—,

[0419] (11′) —O—(CH₂)_(n)—O—,

[0420] (12′) —SO₂—,

[0421] (13′) —(CH₂)_(m)NR^(a12)—(CH₂)_(n)—

[0422] wherein R^(a12) is

[0423] (1″) hydrogen atom,

[0424] (2″) optionally substituted C₁₋₆ alkyl (as defined above),

[0425] (3″) C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0426] (4″) C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the above group B,

[0427] (5″) —COR^(b5)

[0428]  wherein R^(b5) is hydrogen atom, optionally substituted C₁₋₆alkyl (as defined above), C₆₋₁₄ aryl optionally substituted by 1 to 5substituent(s) selected from the above group B or C₆₋₁₄ aryl C₁₋₆ alkyloptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B,

[0429] (6″) —COOR^(b5) (R^(b5) is as defined above) or

[0430] (7″) —SO₂R^(b5) (R^(b5) is as defined above),

[0431] (14′) —NR^(a12)CO— (R^(a12) is as defined above),

[0432] (15′) —CONR^(a13)—(CH₂)_(n)—

[0433] wherein R^(a13) is hydrogen atom, optionally substituted C₁₋₆alkyl (as defined above) or C₆₋₁₄ aryl C₁₋₆ alkyl optionally substitutedby 1 to 5 substituent(s) selected from the above group B,

[0434] (16′) —CONH—CHR^(a14)—

[0435] wherein R^(a14) is C₆₋₁₄ aryl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0436] (17′) —O—(CH)_(m)—CR^(a15)R^(a16)—(CH₂)_(n)—

[0437] wherein R^(a15) and R^(a16) are each independently

[0438] (1″) hydrogen atom,

[0439] (2″) carboxyl,

[0440] (3 “d) C₁₋₆ alkyl,

[0441] (4 ″) —OR^(b6)

[0442] wherein R^(b6) is C₁₋₆ alkyl or C₆₋₁₄ alkyl C₁₋₆ alkyl, or

[0443] (5 ″) —NHR^(b7)

[0444] wherein R^(b7) is hydrogen atom, C₁₋₆ alkyl, C₁₋₆ alkanoyl orC₆₋₁₄ aryl C₁₋₆ alkyloxycarbonyl, or R^(a15) is optionally

[0445] wherein n′, ring B′, Z′ and w′ are the same as theabove-mentioned n, ring B, Z and w, respectively, and may be the same asor different from the respective counterparts,

[0446] (18′) —(CH₂)_(n)—NR^(a12)—CHR^(a15)— (R^(a12) and R^(a15) areeach as defined above),

[0447] (19′) —NR^(a17)SO₂—

[0448] wherein R^(a17) is hydrogen atom or C₁₋₆ alkyl

[0449] or

[0450] (20′) —S(O)_(e)—(CH₂)_(m)—CR^(a15)R^(a16)—(CH₂)_(n)— (e is 0, 1or 2, R^(a15) and R^(a16) are each as defined above).

[0451] (30) The therapeutic agent of (29) above, wherein 1 to 4 of theG¹, G², G³, G⁴, G⁵, G⁶, G⁷, G⁸ and G⁹ is (are) a nitrogen atom.

[0452] (31) The therapeutic agent of (30) above, wherein G² is C(—R²)and G⁶ is a carbon atom.

[0453] (32) The therapeutic agent of (30) or (31) above, wherein G⁵ is anitrogen atom.

[0454] (33) The therapeutic agent of (29) above, wherein, in formula[I], the moiety

[0455] is a fused ring selected from

[0456] (34) The therapeutic agent of (33) above, wherein, in formula[I], the moiety

[0457] is a fused ring selected from

[0458] (35) The therapeutic agent of (34) above, which comprises a fusedring compound of the following formula [I-1]

[0459] wherein each symbol is as defined in (29),

[0460] or a pharmaceutically acceptable salt thereof as an activeingredient.

[0461] (36) The therapeutic agent of (34) above, which comprises a fusedring compound of the following formula [I-2]

[0462] wherein each symbol is as defined in (29),

[0463] or a pharmaceutically acceptable salt thereof as an activeingredient.

[0464] (37) The therapeutic agent of (34) above, which comprises a fusedring compound of the following formula [I-3]

[0465] wherein each symbol is as defined in (29),

[0466] or a pharmaceutically acceptable salt thereof as an activeingredient.

[0467] (38) The therapeutic agent of (34) above, which comprises a fusedring compound of the following formula [I-4]

[0468] wherein each symbol is as defined in (29),

[0469] or a pharmaceutically acceptable salt thereof as an activeingredient.

[0470] (39) The therapeutic agent of any of (29) to (38) above, whereinat least one of R¹, R², R³ and R⁴ is carboxyl, —COOR^(a1),—CONR^(a2)R^(a3) or —SO₂R^(a7) wherein R^(a1), R^(a2), R^(a3) and R^(a7)are as defined in (29).

[0471] (40) The therapeutic agent of any of (29) to (39) above, whereinthe ring Cy is cyclopentyl, cyclohexyl, cycloheptyl ortetrahydrothiopyranyl.

[0472] (41) The therapeutic agent of any of (29) to (40) above, whereinthe ring A is C₆₋₁₄ aryl.

[0473] (42) A fused ring compound of the following formula [II]

[0474] wherein

[0475] the moiety

[0476] is a fused ring selected from

[0477] wherein R¹, R², R³ and R⁴ are each independently,

[0478] (1) hydrogen atom,

[0479] (2) C₁₋₆ alkanoyl,

[0480] (3) carboxyl,

[0481] (4) cyano,

[0482] (5) nitro,

[0483] (6) C₁₋₆ alkyl optionally substituted by 1 to 3 substituent(s)selected from the following group A,

[0484] group A; halogen atom, hydroxyl group, carboxyl, amino, C₁₋₆alkoxy, C₁₋₆ alkoxy C₁₋₆ alkoxy, C₁₋₆ alkoxycarbonyl and C₁₋₆alkylamino,

[0485] (7) —COOR^(a1)

[0486] wherein R^(a1) is optionally substituted C₁₋₆ alkyl (as definedabove), C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the following group B or glucuronic acidresidue,

[0487] group B; halogen atom, cyano, nitro, C₁₋₆ alkyl, halogenated C₁₋₆alkyl, C₁₋₆ alkanoyl, —(CH₂)_(r)—COOR^(b1), —(CH₂)_(r)—CONR^(b1)R^(b2),—(CH₂)_(r)—NR^(b1)R^(b2), —(CH₂)_(r)—NR^(b1)—CO^(b2),—(CH₂)_(r)—NHSO₂R^(b1), —(CH₂)_(r)—OR^(b1), —(CH₂)_(r)—SR^(b1),—(CH₂)_(r)—SO₂R^(b1) and —(CH₂)_(r)—SO₂NR^(b1)R^(b2) wherein R^(b1) andR^(b2) are each independently hydrogen atom or C₁₋₆ alkyl and r is 0 oran integer of 1 to 6,

[0488] (8) —CONR^(a2)R^(a3)

[0489] wherein R^(a2) and R^(a3) are each independently hydrogen atom,C₁₋₆ alkoxy or optionally substituted C₁₋₆ alkyl (as defined above),

[0490] (9) —C(═NR^(a4))NH₂

[0491] wherein R^(a4) is hydrogen atom or hydroxyl group,

[0492] (10) —NHR^(a5)

[0493] wherein R^(a5) is hydrogen atom, C₁₋₆ alkanoyl or C₁₋₆alkylsulfonyl,

[0494] (11) —OR^(a6)

[0495] wherein R^(a6) is hydrogen atom or optionally substituted C₁₋₆alkyl (as defined above),

[0496] (12) —SO₂R^(a7)

[0497] wherein R^(a7) is hydroxyl group, amino, C₁₋₆ alkyl or C₁₋₆alkylamino,

[0498] (13) —P(═O) (OR^(a31))₂

[0499] wherein R^(a31) is hydrogen atom, optionally substituted C₁₋₆alkyl (as defined above) or C₆₋₁₄ aryl C₁₋₆ alkyl optionally substitutedby 1 to 5 substituent(s) selected from the above group B,

[0500] or

[0501] (14) heterocyclic group having 1 to 4 heteroatom(s) selected froman oxygen atom, a nitrogen atom and a sulfur atom, and

[0502] R⁷ is hydrogen atom or optionally substituted C₁₋₆ alkyl (asdefined above),

[0503] ring Cy′ is

[0504] (1) C₃₋₈ cycloalkyl optionally substituted by 1 to 5substituent(s) selected from the following group C, group C; hydroxylgroup, halogen atom, C₁₋₆ alkyl and C₁₋₆ alkoxy, or

[0505] wherein u and v are each independently an integer of 1 to 3,

[0506] ring A′ is a group selected from a group consisting of phenyl,pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, cyclohexyl, cyclohexenyl,furyl and thienyl,

[0507] R^(5′) and R^(6′) are each independently

[0508] (1) hydrogen atom,

[0509] (2) halogen atom,

[0510] (3) optionally substituted C₁₋₆ alkyl (as defined above)

[0511] or

[0512] (4) hydroxyl group

[0513] ring B is

[0514] (1) C₆₋₁₄ aryl,

[0515] (2) C₃₋₈ cycloalkyl or

[0516] (3) heterocyclic group having 1 to 4 heteroatom(s) selected froman oxygen atom, a nitrogen atom and a sulfur atom,

[0517] each Z is independently

[0518] (1) a group selected from the following group D

[0519] (2) C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the following group D,

[0520] (3) C₃₋₈ cycloalkyl optionally substituted by 1 to 5substituent(s) selected from the following group D,

[0521] (4) C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the following group D,

[0522] (5) heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the following group D wherein theheterocyclic group has 1 to 4 heteroatom(s) selected from an oxygenatom, a nitrogen atom and a sulfur atom, or

[0523] (6) heterocycle C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the following group D wherein theheterocycle C₁₋₆ alkyl is C₁₋₆ alkyl substituted by heterocyclic groupoptionally substituted by 1 to 5 substituent(s) selected from the groupD, as defined above, group D:

[0524] (a) hydrogen atom,

[0525] (b) halogen atom,

[0526] (c) cyano,

[0527] (d) nitro,

[0528] (e) optionally substituted C₁₋₆ alkyl (as defined above),

[0529] (f) —(CH₂)_(t)—COR^(a18),

[0530] (hereinafter each t means independently 0 or an integer of 1 to6),

[0531] wherein R^(a18) is

[0532] (1′) optionally substituted C₁₋₆ alkyl (as defined above),

[0533] (2′) C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the above group B or

[0534] (3′) heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B wherein the heterocyclicgroup has 1 to 4 heteroatom(s) selected from an oxygen atom, a nitrogenatom and a sulfur atom,

[0535] (g) —(CH₂)_(t)—COOR^(a19)

[0536] wherein R^(a19) is hydrogen atom, optionally substituted C₁₋₆alkyl (as defined above) or C₆₋₁₄ aryl C₁₋₆ alkyl optionally substitutedby 1 to 5 substituent(s) selected from the above group B,

[0537] (h) —(CH₂)_(t)—CONR^(a27)R^(a28)

[0538] wherein R^(a27) and R^(a28) are each independently,

[0539] (1″) hydrogen atom,

[0540] (2″) optionally substituted C₁₋₆ alkyl (as defined above),

[0541] (3″) C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the above group B,

[0542] (4″) C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0543] (5″) heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0544] (6″) heterocycle C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0545]  wherein the heterocycle C₁₋₆ alkyl is C₁₋₆ alkyl substituted byheterocyclic group optionally substituted by 1 to 5 substituent(s)selected from the above group B, as defined above,

[0546] (7″) C₃₋₈ cycloalkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0547] (8″) C₃₋₈ cycloalkyl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0548] (9″) hydroxyl group or

[0549] (10″) C₁₋₆ alkoxy,

[0550] (i) (CH₂)_(t)—C(═NR^(a33) )NH₂

[0551] wherein R^(a33) is hydrogen atom, C₁₋₆ alkyl, hydroxyl group orC₁₋₆ alkoxy,

[0552] (j) —(CH₂)_(t)—OR^(a20)

[0553] wherein R^(a20) is

[0554] (1′) hydrogen atom,

[0555] (2′) optionally substituted C₁₋₆ alkyl (as defined above),

[0556] (3′) optionally substituted C₂₋₆ alkenyl (as defined above),

[0557] (4′) C₂₋₆ alkynyl optionally substituted by 1 to 3 substituent(s)selected from the above group A,

[0558] (5′) C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the above group B,

[0559] (6′) C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0560] (7′) heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0561] (8′) heterocycle C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0562] (9′) C₃₋₈ cycloalkyl optionally substituted by 1 to 5substituent(s) selected from the above group B, or

[0563] (10′) C₃₋₈ cycloalkyl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0564] (k) —(CH₂)_(t)—O—(CH₂)_(p)—COR^(a21)

[0565] wherein R^(a21) is amino, C₁₋₆ alkylamino or heterocyclic groupoptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B,

[0566] and p is 0 or an integer of 1 to 6,

[0567] (l) —(CH₂)_(t)—NR^(a22)R^(a23)

[0568] wherein R^(a22) and R^(a23) are each independently

[0569] (1′) hydrogen atom,

[0570] (2′) optionally substituted C₁₋₆ alkyl (as defined above),

[0571] (3′) C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the above group B,

[0572] (4′) C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0573] (5′) heterocycle C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group, B or

[0574] (6′) heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0575] (m) —(CH₂)_(t)—NR^(a29)CO—R^(a24)

[0576] wherein R^(a29) is hydrogen atom, C₁₋₆ alkyl or C₁₋₆ alkanoyl,and

[0577] R^(a24) is

[0578] (1′) amino,

[0579] (2′) C₁₋₆ alkylamino,

[0580] (3′) optionally substituted C₁₋₆ alkyl (as defined above),

[0581] (4′) C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the above group B,

[0582] (5′) heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B, or

[0583] (6′) heterocycle C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0584] (n) —(CH₂)_(t)—NR^(a29)SO₂—R^(a25)

[0585] wherein R^(a29) is as defined above, and R^(a25) is hydrogenatom, optionally substituted C₁₋₆ alkyl (as defined above), C₆₋₁₄ aryloptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B or heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0586] (o) —(CH₂)_(t)—S(O)_(q)—R^(a25)

[0587] wherein R^(a25) is as defined above, and q is 0, 1 or 2,

[0588] (p) —(CH₂)_(t)—SO₂—NHR^(a26)

[0589] wherein R^(a26) is hydrogen atom, optionally substituted C₁₋₆alkyl (as defined above), C₆₋₁₄ aryl optionally substituted by 1 to 5substituent(s) selected from the above group B

[0590] or heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0591] and

[0592] (q) heterocyclic group having 1 to 4 heteroatom(s) selected froman oxygen atom, a nitrogen atom and a sulfur atom,

[0593] w is an integer of 1 to 3, and

[0594] Y is

[0595] (1) a single bond,

[0596] (2) C₁₋₆ alkylene,

[0597] (3) C₂₋₆ alkenylene,

[0598] (4) —(CH₂)_(m)—O—(CH₂)_(n)—,

[0599] (hereinafter m and n are each independently 0 or an integer of 1to 6),

[0600] (5) —CO—,

[0601] (6) —CO₂—(CH₂)_(n)—,

[0602] (7) —CONH—(CH₂)_(n)—NH—,

[0603] (8) —NHCO₂—,

[0604] (9) —NHCONH—,

[0605] (10) —O—(CH₂)_(n)—CO—,

[0606] (11) —O—(CH₂)_(n)—O—,

[0607] (12) —SO₂—,

[0608] (13) —(CH₂)_(m)NR^(a12)—(CH₂)_(n)—

[0609] wherein R^(a12) is

[0610] (1′) hydrogen atom,

[0611] (2′) optionally substituted C₁₋₆ alkyl (as defined above),

[0612] (3′) C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0613] (4′) C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the above group B,

[0614] (5) —COR^(b5)

[0615] wherein R^(b5) is hydrogen atom, optionally substituted C₁₋₆alkyl (as defined above), C₆₋₁₄ aryl optionally substituted by 1 to 5substituent(s) selected from the above group B or C₆₋₁₄ aryl C₁₋₆ alkyloptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B,

[0616] (6′) —COOR^(b5) (R^(b5) is as defined above) or

[0617] (7′) —SO₂R^(b5) (R^(b5) is as defined above),

[0618] (14) —NR^(a12)CO— (R^(a12) is a s defined above),

[0619] (15) —CONR^(a13)—(CH₂)_(n)—

[0620] wherein R^(a13) is hydrogen atom, optionally substituted C₁₋₆alkyl (as defined above) or C₆₋₁₄ aryl C₁₋₆ alkyl optionally substitutedby 1 to 5 substituent(s) selected from the above group B,

[0621] (16) —CONH—CHR^(a14)—

[0622] wherein R^(a14) is C₆₋₁₄ aryl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0623] (17) —O—(CH₂)_(m)CR^(a15)R^(a16)—(CH₂)_(n)—

[0624] wherein R^(a15) and R^(a16) are each independently

[0625] (1′) hydrogen atom,

[0626] (2′) carboxyl,

[0627] (3′) C₁₋₆ alkyl,

[0628] (4′) —OR^(b6)

[0629] wherein R^(b6) is C₁₋₆ alkyl or C₆₋₁₄ aryl C₁₋₆ alkyl, or

[0630] (5′) —NHR^(b7)

[0631] wherein R^(b7) is hydrogen atom, C₁₋₆ alkyl, C₁₋₆ alkanoyl orC₆₋₁₄ aryl C₁₋₆ alkyloxycarbonyl,

[0632] or

[0633] R^(a15) is optionally

[0634] wherein n′, ring B′, Z′ and w′ are the same as theabove-mentioned n, ring B, Z and w, respectively, and may be the same asor different from the respective counterparts,

[0635] (18) —(CH₂)_(n)—NR^(a12)—CHR^(a15)—(R^(a12) and R^(a15) are eachas defined above),

[0636] (19) —NR^(a17)SO₂—wherein R^(a17) is hydrogen atom or C₁₋₆ alkyl,

[0637] (20) —S(O)_(e)—(CH₂)_(m)—CR^(a15)R^(a16)—(CH₂)_(n)— (e is 0, 1 or2, R^(a15) and R^(a16) are each as defined above),

[0638] or

[0639] (21) —(CH₂)_(m)—CR^(a15)R^(a16)—(CH₂ )—(R^(a15) and R^(a16) areeach as defined above),

[0640] or a pharmaceutically acceptable salt thereof.

[0641] (43) The fused ring compound of (42) above, which is representedby the following formula [II-1]

[0642] wherein each symbol is as defined in (42),

[0643] or a pharmaceutically acceptable salt thereof.

[0644] (44) The fused ring compound of (42) above, which is representedby the following formula [II-2]

[0645] wherein each symbol is as defined in (42),

[0646] or a pharmaceutically acceptable salt thereof.

[0647] (45) The fused ring compound of (42) above, which is representedby the following formula [II-3]

[0648] wherein each symbol is as defined in (42),

[0649] or a pharmaceutically acceptable salt thereof.

[0650] (46) The fused ring compound of (42) above, which is representedby the following formula [II-4]

[0651] wherein each symbol is as defined in (42),

[0652] or a pharmaceutically acceptable salt thereof.

[0653] (47) The fused ring compound of any of (42) to (46) above,wherein at least one of R¹, R², R³ and R⁴ is carboxyl, —COOR^(a1),—CONR^(a2)R^(a3), —SO₂R^(a7) (wherein R^(a1), R^(a2), R^(a3) and R^(a7)are as defined in (42)),

[0654] or a pharmaceutically acceptable salt thereof.

[0655] (48) The fused ring compound of (47) above, wherein at least oneof R¹, R², R³ and R⁴ is carboxyl, —COOR^(a1) or —SO₂R^(a7) whereinR^(a1) and R^(a7) are as defined in (42), or a pharmaceuticallyacceptable salt thereof.

[0656] (49) The fused ring compound of (48) above, wherein at least oneof R¹, R², R³ and R⁴ is carboxyl or —COOR^(a1) wherein R^(a1) is asdefined in (42), or a pharmaceutically acceptable salt thereof.

[0657] (50) The fused ring compound of (49) above, wherein R² iscarboxyl and R¹, R³ and R⁴ are hydrogen atoms, or a pharmaceuticallyacceptable salt thereof.

[0658] (51) The fused ring compound of any of (42) to (46) above,wherein at least one of R¹, R², R³ and R⁴ is carboxyl or —COOR^(a1)wherein R^(a1) is glucuronic acid residue, or a pharmaceuticallyacceptable salt thereof.

[0659] (52) The fused ring compound of any of (42) to (46) above,wherein at least one of R¹, R², R³ and R⁴ is heterocyclic group having 1to 4 heteroatom(s) selected from an oxygen atom, a nitrogen atom and asulfur atom, or a pharmaceutically acceptable salt thereof.

[0660] (53) The fused ring compound of any of (42) to (52) above,wherein the ring Cy′ is cyclopentyl, cyclohexyl, cycloheptyl ortetrahydrothiopyranyl, or a pharmaceutically acceptable salt thereof.

[0661] (54) The fused ring compound of (42) above, wherein the ring Cy′is cyclopentyl, cyclohexyl or cycloheptyl, or a pharmaceuticallyacceptable salt thereof.

[0662] (55) The fused ring compound of any of (42) to (52) above,wherein the ring Cy′ is

[0663] wherein each symbol is as defined in (42), or a pharmaceuticallyacceptable salt thereof.

[0664] (56) The fused ring compound of any of (42) to (55) above,wherein the ring A′ is phenyl, pyridyl, pyrazinyl, pyrimidinyl orpyridazinyl, or a pharmaceutically acceptable salt thereof.

[0665] (57) The fused ring compound of (56) above, wherein the(ring A′is phenyl or pyridyl, or a pharmaceutically acceptable salt thereof.

[0666] (58) The fused ring compound of (57) above, wherein the ring A′is phenyl, or a pharmaceutically acceptable salt thereof.

[0667] (59) The fused ring compound of any of (42) to (58) above,wherein at least one substituent optionaly substituted by group A is asubstituent substituted by C₁₋₆ alkoxy C₁₋₆ alkoxy, or apharmaceutically acceptable salt thereof.

[0668] (60) The fused ring compound of any of (42) to (59) above,wherein the Y is —(CH₂)_(m)—O—(CH₂)_(n)—, —NHCO₂—, —CONH—CHR^(a14)—,—(CH₂)_(m)—NR^(a12)—(CH₂)_(n)—, —CONR^(a13)—(CH₂)_(n),—O—(CH₂)_(m)—CR^(a15)R^(a16)—(CH₂)_(n)— or—(CH₂)_(n)—NR^(a12)—CHR^(a15)— (wherein each symbol is as defined in(42)),

[0669] or a pharmaceutically acceptable salt thereof.

[0670] (61) The fused ring compound of (42) above, wherein the Y is—(CH₂)_(m)—O—(CH₂)_(n)— or —O—(CH₂)_(m)—CR^(a15)R^(a16)—(CH₂)_(n)—(wherein each symbol is as defined in (42)), or a pharmaceuticallyacceptable salt thereof.

[0671] (62) The fused ring compound of (61) above, wherein the Y is—(CH₂)_(m)—O—(CH₂)_(n)— wherein each symbol is as defined in (42), or apharmaceutically acceptable salt thereof.

[0672] (63) The fused ring compound of any of (42) to (59) above,wherein the Y is —(CH₂)_(m)—CR^(a15)R^(a16)—(CH₂)_(n)— (wherein eachsymbol is as defined in (42)), or a pharmaceutically acceptable saltthereof.

[0673] (64) The fused ring compound of any of (42) to (63) above,wherein the R² is carboxyl, R¹, R³ and R⁴ are hydrogen atoms, the ringCy′ is cyclopentyl, cyclohexyl or cycloheptyl, and the ring A′ isphenyl, or a pharmaceutically acceptable salt thereof.

[0674] (65) The fused ring compound of any of (42) to (64) above,wherein at least one group represented by Z is heterocycle C₁₋₆ alkyloptionally substituted by 1 to 5 substituent(s) selected from the groupD, or a pharmaceutically acceptable salt thereof.

[0675] (66) The fused ring compound of any of (42) to (64) above,wherein at least one group represented by Z is heterocyclic groupoptionally substituted by 1 to 5 substituent(s) selected from the groupD, wherein said heterocyclic group is selected from the followinggroups:

[0676] wherein E¹ is an oxygen atom, a sulfur atom or N(—R^(a35)), E² isan oxygen atom, CH₂ or N(—R^(a35)), E³ is an oxygen atom or a sulfuratom, wherein each R^(a35) is independently hydrogen atom or C₁₋₆ alkyl,f is an integer of 1 to 3, and h and h′ are the same or different andeach is an integer of 1 to 3, or a pharmaceutically acceptable saltthereof.

[0677] (67) The fused ring compound of (66) above, wherein at least onegroup represented by Z is heterocyclic group optionally substituted by 1to 5 substituent(s) selected from the group D, wherein said heterocyclicgroup is selected from the following groups:

[0678] wherein each symbol is as defined in (66), or a pharmaceuticallyacceptable salt thereof.

[0679] (68) The fused ring compound of any of (42) to (64) above,wherein at least one group represented by group D is—(CH₂)_(t)—CONR^(a27)R^(a28) wherein each symbol is as defined in (42),and at least one of R^(a27) and R^(a28) is C₁₋₆ alkoxy, or apharmaceutically acceptable salt thereof.

[0680] (69) The fused ring compound of any of (42) to (64) above,wherein at least one group represented by group D is—(CH₂)_(t)—C(═NR^(a33) )NH₂ wherein each symbol is as defined in (42),and R^(a33) is hydroxyl group or C₁₋₆ alkoxy, or a pharmaceuticallyacceptable salt thereof.

[0681] (70) The fused ring compound of any of (42) to (64) above,wherein at least one group represented by group D is—(CH₂)_(t)—O—(CH₂)_(p)—COR^(a21) wherein each symbol is as defined in(42), and R^(a21) is amino, or a pharmaceutically acceptable saltthereof.

[0682] (71) The fused ring compound of any of (42) to (64) above,wherein at least one group represented by group D is—(CH₂)_(t)—NR^(a29)CO—R^(a24) wherein each symbol is as defined in (42),and R^(a24) is amino or

[0683] C₁₋₆ alkylamino, or a pharmaceutically acceptable salt thereof.

[0684] (72) The fused ring compound of any of (42) to (64) above,wherein at least one group represented by group D is—(CH₂)_(t)—NR^(a22)R^(a23) wherein each symbol is as defined in (42),and at least one of R^(a22) and R^(a23) is heterocyclic group optionallysubstituted by 1 to 5 substituent(s) selected from the group B, or apharmaceutically acceptable salt thereof.

[0685] (73) The fused ring compound of any of (42) to (64) above,wherein at least one group represented by group D is heterocyclic grouphaving 1 to 4 heteroatom(s) selected from an oxygen atom, a nitrogenatom and a sulfur atom, or a pharmaceutically acceptable salt thereof.

[0686] (74) The fused ring compound of (42) above, which is representedby the following formula [II]

[0687] wherein

[0688] the moiety

[0689] is a fused ring selected from

[0690] wherein R¹, R², R³ and R⁴ are each independently,

[0691] (1) hydrogen atom,

[0692] (2) C₁₋₆ alkanoyl,

[0693] (3) carboxyl,

[0694] (4) cyano,

[0695] (5) nitro,

[0696] (6) C₁₋₆ alkyl optionally substituted by 1 to 3 substituent(s)selected from the following group A,

[0697] group A; halogen atom, hydroxyl group, carboxyl, amino, C₁₋₆alkoxy, C₁₋₆ alkoxycarbonyl and C₁₋₆ alkylamino,

[0698] (7) —COOR^(a1)

[0699] wherein R^(a1) is optionally substituted C₁₋₆ alkyl (as definedabove) or C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the following group B,

[0700] group B; halogen atom, cyano, nitro, C₁₋₆ alkyl, halogenated C₁₋₆alkyl, C₁₋₆ alkanoyl, —(CH₂)_(r)—COOR^(b1), —(CH₂)_(r)—CONR^(b1)R^(b2),—(CH₂)_(r)—NR^(b1)R^(b2), —(CH₂)_(r)NR^(b1)—COR^(b2),—(CH₂)_(r)—NHSO₂R^(b1), (CH₂)_(r)—OR^(b1), —(CH₂)_(r)—SR^(b1),—(CH₂)_(r)—SO₂R^(b1) and —(CH₂)_(r)—SO₂NR^(b1)R^(b2) wherein R^(b1) andR^(b2) are each independently hydrogen atom or C₁₋₆ alkyl and r is 0 oran integer of 1 to 6,

[0701] (8) —CONR^(a2)R^(a3)

[0702] wherein R^(a2) and R^(a3) are each independently hydrogen atom,C₁₋₆ alkoxy or optionally substituted C₁₋₆ alkyl (as defined above),

[0703] (9) —C(═NR^(a4))NH₂

[0704] wherein R^(a4) is hydrogen atom or hydroxyl group,

[0705] (10) —NHR^(a5)

[0706] wherein R^(a5) is hydrogen atom, C₁₋₆ alkanoyl or C₁₋₆alkylsulfonyl,

[0707] (11) —OR^(a6)

[0708] wherein R^(a6) is hydrogen atom or optionally substituted C₁₋₆alkyl (as defined above),

[0709] (12) —SO₂R^(a7)

[0710] wherein R^(a7) is hydroxyl group, amino, C₁₋₆ alkyl or C₁₋₆alkylamino

[0711] or

[0712] (13) —P(═O) (OR^(a31))₂

[0713] wherein R^(a31) is hydrogen atom, optionally substituted C₁₋₆alkyl (as defined above) or C₆₋₁₄ aryl C₁₋₆ alkyl optionally substitutedby 1 to 5 substituent(s) selected from the above group B, and

[0714] R⁷ is hydrogen atom or optionally substituted

[0715] C₁₋₆ alkyl (as defined above),

[0716] ring Cy′ is

[0717] (1) C₃₋₈ cycloalkyl optionally substituted by 1 to 5substituent(s) selected from the following group C, group C; hydroxylgroup, halogen atom, C₁₋₆ alkyl and C₁₋₆ alkoxy, or

[0718] wherein u and v are each independently an integer of 1 to 3,

[0719] ring A′ is a group selected from a group consisting of phenyl,pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, cyclohexyl, cyclohexenyl,furyl and thienyl,

[0720] R^(5′) and R^(6′) are each independently

[0721] (1) hydrogen atom,

[0722] (2) halogen atom,

[0723] (3) optionally substituted C₁₋₆ alkyl (as defined above)

[0724] or

[0725] (4) hydroxyl group

[0726] ring B is

[0727] (1) C₆₋₁₄ aryl,

[0728] (2) C₃₋₈ cycloalkyl or

[0729] (3) heterocyclic group having 1 to 4 heteroatom(s) selected froman oxygen atom, a nitrogen atom and a sulfur atom,

[0730] each Z is independently

[0731] (1) a group selected from the following group D,

[0732] (2) C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the following group D,

[0733] (3) C₃₋₈ cycloalkyl optionally substituted by 1to 5substituent(s) selected from the following group D,

[0734] (4) C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the following group D or

[0735] (5) heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the following group D wherein theheterocyclic group has 1 to 4 heteroatom(s) selected from an oxygenatom, a nitrogen atom and a sulfur atom,

[0736] group D:

[0737] (a) hydrogen atom,

[0738] (b) halogen atom,

[0739] (c) cyano,

[0740] (d) nitro,

[0741] (e) optionally substituted C₁₋₆ alkyl (as defined above),

[0742] (f) —(CH₂)_(t)—COR^(a18),

[0743] (hereinafter each t means independently 0 or an integer of 1 to6),

[0744] wherein R^(a18) is

[0745] (1′) optionally substituted C₁₋₆ alkyl (as defined above),

[0746] (2′) C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the above group B or

[0747] (3′) heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B wherein the heterocyclicgroup has 1 to 4 heteroatom(s) selected from an oxygen atom, a nitrogenatom and a sulfur atom,

[0748] (g) —(CH₂)_(t)—COOR^(a19)

[0749] wherein R^(a19) is hydrogen atom, optionally substituted C₁₋₆alkyl (as defined above) or C₆₋₁₄ aryl C₁₋₆ alkyl optionally substitutedby 1 to 5 substituent(s) selected from the above group B,

[0750] (h) —(CH₂)_(t)—CONR^(a27)R^(a28)

[0751] wherein R^(a27) and R^(a28) are each independently,

[0752] (1″) hydrogen atom,

[0753] (2″) optionally substituted C₁₋₆ alkyl (as defined above),

[0754] (3″) C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the above group B,

[0755] (4″) C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0756] (5″) heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0757] (6″) heterocycle C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0758]  wherein the heterocycle C₁₋₆ alkyl is C₁₋₆ alkyl substituted byheterocyclic group optionally substituted by 1 to 5 substituent(s)selected from the above group B, as defined above,

[0759] (7″) C₃₋₈ cycloalkyl optionally substituted by 1 to 5substituent(s) selected from the above group B, or

[0760] (8″) C₃₋₈ cycloalkyl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0761] (i) —(CH₂)_(t)—C(′NR^(a33))NH₂

[0762] wherein R^(a33) is hydrogen atom or C₁₋₆ alkyl,

[0763] (j) —(CH₂)_(t)—OR^(a20)

[0764] wherein R^(a20) is

[0765] (1′) hydrogen atom,

[0766] (2′) optionally substituted C₁₋₆ alkyl (as defined above),

[0767] (3′) optionally substituted C₂₋₆ alkenyl (as defined above),

[0768] (4′) C₂₋₆ alkynyl optionally substituted by 1 to 3 substituent(s)selected from the above group A,

[0769] (5′) C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the above group B,

[0770] (6′) C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0771] (7′) heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0772] (8′) heterocycle C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0773] (9′) C₃₋₈ cycloalkyl optionally substituted by 1 to 5substituent(s) selected from the above group B, or

[0774] (10′) C₃₋₈ cycloalkyl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0775] (k) —(CH₂)_(t)—O—(CH₂)_(p)—COR^(a21)

[0776] wherein R^(a21) is C₁₋₆ alkylamino or heterocyclic groupoptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B,

[0777] and p is 0 or an integer of 1 to 6,

[0778] (l) —(CH₂)_(t)—NR^(a22)R^(a23)

[0779] wherein R^(a22) and R²³ are each independently

[0780] (1′) hydrogen atom,

[0781] (2′) optionally substituted C₁₋₆ alkyl (as defined above),

[0782] (3′) C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the above group B,

[0783] (4′) C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B or

[0784] (5′) heterocycle C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0785] (m) —(CH₂)_(t)—NR^(a29)COR^(a24)

[0786] wherein R^(a29) is hydrogen atom, C₁₋₆ alkyl or C₁₋₆ alkanoyl,R^(a24) is optionally substituted C₁₋₆ alkyl (as defined above), C₆₋₁₄aryl optionally substituted by 1 to 5 substituent(s) selected from theabove group B or heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0787] (n) —(CH₂)_(t)—NHSO₂—R^(a25)

[0788] wherein R^(a25) is hydrogen atom, optionally substituted C₁₋₆alkyl (as defined above), C₆₋₁₄ aryl optionally substituted by 1 to 5substituent(s) selected from the above group B

[0789] or heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0790] (o) —(CH₂)_(t)—S(O)_(q)—R^(a25)

[0791] wherein R^(a25) is as defined above, and q is 0, 1 or 2,

[0792] and

[0793] (p) —(CH₂)_(t)—SO₂—NHR^(a26)

[0794] wherein R^(a26) is hydrogen atom, optionally substituted C₁₋₆alkyl (as defined above), C₆₋₁₄ aryl optionally substituted by 1 to 5substituent(s) selected from the above group B or heterocyclic groupoptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B,

[0795] w is an integer of 1 to 3, and

[0796] Y is

[0797] (1) a single bond,

[0798] (2) C₁₋₆ alkylene,

[0799] (3) C₂₋₆ alkenylene,

[0800] (4) —(CH₂)_(m)—O—(CH₂)_(n)—,

[0801] (hereinafter m and n are each independently 0 or an integer of 1to 6),

[0802] (5) —CO—,

[0803] (6) —CO₂—(CH₂)_(n)—,

[0804] (7) —CONH—(CH₂)_(n)—NH—,

[0805] (8) —NHCO₂—,

[0806] (9) —NHCONH—,

[0807] (10) —O—(CH₂)_(n)—CO—,

[0808] (11) —O—(CH₂)_(n)—O—,

[0809] (12) —SO₂—,

[0810] (13) —(CH₂)_(m)NR^(a12)—(CH₂)_(n)—

[0811] wherein R^(a12) is

[0812] (1′) hydrogen atom,

[0813] (2′) optionally substituted C₁₋₆ alkyl (as defined above),

[0814] (3′) C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0815] (4′) C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the above group B,

[0816] (5′) —COR^(b5)

[0817] wherein R^(b5) is hydrogen atom, optionally substituted C₁₋₆alkyl (as defined above), C₆₋₁₄ aryl optionally substituted by 1 to 5substituent(s) selected from the above group B or C₆₋₁₄ aryl C₁₋₆ alkyloptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B,

[0818] (6′) —COOR^(b5) (R^(b5) is as defined above) or

[0819] (7′) —SO₂R^(b5) (R^(b5) is as defined above),

[0820] (14) —NR CO— (R is as defined above),

[0821] (15) —CONR^(a13)—(CH₂)_(n)—

[0822] wherein R^(a13) is hydrogen atom, optionally substituted C₁₋₆alkyl (as defined above) or C₆₋₁₄ aryl C₁₋₆ alkyl optionally substitutedby 1 to 5 substituent(s) selected from the above group B,

[0823] (16) —CONH—CHR^(a14)—

[0824] wherein R^(a14) is C₆₋₁₄ aryl optionally substituted by 1 to 5substituent(s) selected from the above group B,

[0825] (17) —O—(CH₂)_(m)CR^(a15)R^(a16)—(CH₂)_(n)—

[0826] wherein R^(a15) and R^(a16) are each independently

[0827] (1′) hydrogen atom,

[0828] (2′) carboxyl,

[0829] (3′) C₁₋₆ alkyl,

[0830] (4′) —OR^(b6)

[0831] wherein R^(b6) is C₁₋₆ alkyl or C₆₋₁₄ aryl C₁₋₆ alkyl,

[0832] or

[0833] (5′) —NHR^(b7)

[0834] wherein R^(b7) is hydrogen atom, C₁₋₆ alkyl, C₁₋₆ alkanoyl orC₆₋₁₄ aryl C₁₋₆ alkyloxycarbonyl, or R^(a15) is optionally

[0835]  wherein n′, ring B′, Z′ and w′ are the same as theabove-mentioned n, ring B, Z and w, respectively, and may be the same asor different from the respective counterparts,

[0836] (18) —(CH₂)_(n)—NR^(a12)—CHR^(a15)— (R^(a12) and R^(a15) each asdefined above),

[0837] (19) —NR^(a17)SO₂—

[0838] wherein R^(a17) is hydrogen atom or C₁₋₆ alkyl

[0839] or

[0840] (20) —S(O)_(e)—(CH₂)_(m)—CR^(a15)R^(a16)—(CH₂)_(n)— (e is 0, 1 or2, R^(a15) and R^(a16) are each as defined above)

[0841] or a pharmaceutically acceptable salt thereof.

[0842] (75) The fused ring compound of (74) above, which is representedby the following formula [II-1]

[0843] wherein each symbol is as defined in (74),

[0844] or a pharmaceutically acceptable salt thereof.

[0845] (76) The fused ring compound of (74) above, which is r(presentedby the following formula [II-2]

[0846] wherein each symbol is as defined in (74),

[0847] or a pharmaceutically acceptable salt thereof.

[0848] (77) The fused ring compound of (74) above, which is representedby the following formula [II-3]

[0849] wherein each symbol is as defined in (74),

[0850] or a pharmaceutically acceptable salt thereof.

[0851] (78) The fused ring compound of (74) above, which is representedby the following formula [II-4]

[0852] wherein each symbol is as defined in (74),

[0853] or a pharmaceutically acceptable salt thereof.

[0854] (79) The fused ring compound of any of (74) to (78) above,wherein at least one of R¹, R², R³ and R⁴ is carboxyl, —COOR^(a1) or—SO₂R^(a7) wherein R^(a1) and R^(a7) are as defined in (74), or apharmaceutically acceptable salt thereof.

[0855] (80) The fused ring compound of (79) above, wherein at least oneof R¹, R², R³ and R⁴ is carboxyl or —COOR^(a1) wherein R^(a1) is asdefined in (74), or a pharmaceutically acceptable salt thereof.

[0856] (81) The fused ring compound of (80) above, wherein R² iscarboxyl and R¹, R³ and R⁴ are hydrogen atoms, or a pharmaceuticallyacceptable salt thereof.

[0857] (82) The fused ring compound of any of (74) to (81) above,wherein the ring Cy′ is cyclopentyl, cyclohexyl, cycloheptyl ortetrahydrothiopyranyl, or a pharmaceutically acceptable salt thereof.

[0858] (83) The fused ring compound of (82) above, wherein the ring Cy′is cyclopentyl, cyclohexyl or cycloheptyl, or a pharmaceuticallyacceptable salt thereof.

[0859] (84) The fused ring compound of any of (74) to (83) above,wherein the ring A′ is phenyl, pyridyl, pyrazinyl, pyrimidinyl orpyridazinyl, or a pharmaceutically acceptable salt thereof.

[0860] (85) The fused ring compound of (84) above, wherein the ring A′is phenyl or pyridyl, or a pharmaceutically acceptable salt thereof.

[0861] (86) The fused ring compound of (85) above, wherein the ring A′is phenyl, or a pharmaceutically acceptable salt thereof.

[0862] (87) The fused ring compound of any of (74) to (86) above,wherein the Y is —(CH₂)_(m)—O—(CH₂)_(n)—, —NHCO₂—, —CONH—CHR^(a14)—,—(CH₂)_(m)—NR^(a12)—(CH₂)_(n)—, —CONR^(a13)—(CH₂)_(n)—,—O—(CH₂)_(m)CR^(a15)R^(a16)—(CH₂)_(n)— or —(CH₂)_(n)—NR^(a12)—CHR^(a15)—(wherein each symbol is as defined in (74)), or a pharmaceuticallyacceptable salt thereof.

[0863] (88) The fused ring compound of (87) above, wherein the Y is—(CH₂)_(m)—O—(CH₂)_(n)— or —O—(CH₂)_(m)—CR^(a15)R^(a16)—(CH₂)_(n)—(wherein each symbol is as defined in (74)), or a pharmaceuticallyacceptable salt thereof.

[0864] (89) The fused ring compound of (88) above, wherein thus Y is—(CH₂)_(m)—O—(CH₂)_(n)— wherein each symbol is as defined in (74), or apharmaceutically acceptable salt thereof.

[0865] (90) The fused ring compound of any of (74) to (89) above,wherein the R² is carboxyl, R¹, R³ and R⁴ are hydrogen atoms, the ringCy′ is cyclopentyl, cyclohexyl or cycloheptyl, and the ring A′ isphenyl, or a pharmaceutically acceptable salt thereof.

[0866] (91) The fused ring compound of the formula [I] or apharmaceutically acceptable salt thereof, which is selected from thegroup consisting of

[0867] ethyl2-[4-(3-bromophenoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylate(Example 1),

[0868]2-[4-(3-bromophenoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylic acid(Example 2),

[0869] ethyl 1-cyclohexyl-2-(4-hydroxyphenyl)benzimidazole-5-carboxylate(Example 3),

[0870] ethyl2-[4-(2-bromo-5-chlorobenzyloxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylate(Example 4),

[0871] ethyl2-{4-[2-(4-chlorophenyl)-5-chlorobenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylate(Example 5),

[0872]2-{4-[2-(4-chlorophenyl)-5-chlorobenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 6),

[0873] ethyl2-[4-(2-bromo-5-methoxybenzyloxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylate(Example 7),

[0874] ethyl2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylate(Example 8),

[0875]2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 9),

[0876] ethyl1-cyclohexyl-2-{4-[(E)-2-phenylvinyl]phenyl}benzimidazole-5-carboxylate(Example 10),

[0877]1-cyclohexyl-2-{4-[(E)-2-phenylvinyl]phenyl}benzimidazole-5-carboxylicacid (Example 11),

[0878] 2-(4-benzyloxyphenyl)-1-cyclopentylbenzimidazole-5-carboxylicacid (Example 12),

[0879] 2-(4-benzyloxyphenyl)-1-cyclopentylbenzimidazole-5-carboxamide(Example 13),

[0880] 2-(4-benzyloxyphenyl)-5-cyano-1-cyclopentylbenzimidazole (Example14),

[0881] 2-(4-benzyloxyphenyl)-1-cyclopentylbenzimidazole-5-carboxamideoxime (Example 15),

[0882] ethyl1-cyclohexyl-2-{4-[{4-(4-fluorophenyl)-2-methyl-5-thiazolyl}methoxy]phenyl}benzimidazole-5-carboxylate(Example 16),

[0883]1-cyclohexyl-2-{4-[{4-(4-fluorophenyl)-2-methyl-5-thiazolyl}-methoxy]phenyl}benzimidazole-5-carboxylicacid (Example 17),

[0884] ethyl1-cyclohexyl-2-(2-fluoro-4-hydroxyphenyl)benzimidazole-5-carboxylate(Example 18),

[0885] ethyl2-{4-[bis(3-fluorophenyl)methoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylate(Example 19),

[0886]2-{4-[bis(3-fluorophenyl)methoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 20),

[0887] ethyl 1-cyclopentyl-2-(4-nitrophenyl)benzimidazole-5-carboxylate(Example 21),

[0888] ethyl 2-(4-aminophenyl)-1-cyclopentylbenzimidazole-5-carboxylate(Example 22),

[0889] ethyl2-(4-benzoylaminophenyl)-1-cyclopentylbenzimidazole-5-carboxylate(Example 23),

[0890] 2-(4-benzoylaminophenyl)-1-cyclopentylbenzimidazole-5-carboxylicacid (Example 24),

[0891] ethyl2-{4-[3-(3-chlorophenyl)phenoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylate(Example 25),

[0892]2-{4-[3-(3-chlorophenyl)phenoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 26),

[0893] ethyl2-[4-(3-acetoxyphenyloxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylate(Example 27),

[0894] ethyl1-cyclohexyl-2-[4-(3-hydroxyphenyloxy)phenyl]-benzimidazole-5-carboxylate(Example 28),

[0895] ethyl1-cyclohexyl-2-{4-[3-(4-pyridylmethoxy)phenyloxy]phenyl}-benzimidazole-5-carboxylate(Example 29),

[0896]1-cyclohexyl-2-{4-[3-(4-pyridylmethoxy)phenyloxy]phenyl}-benzimidazole-5-carboxylicacid (Example 30),

[0897] 2-(4-benzyloxyphenyl)-1-cyclopentylbenzimidazole (Example 31),

[0898] ethyl2-(4-benzyloxyphenyl)-1-cyclopentylbenzimidazole-5-carboxylate (Example32),

[0899]2-(4-benzyloxyphenyl)-1-cyclopentyl-N,N-dimethylbenzimidazole-5-carboxamide(Example 33),

[0900]2-(4-benzyloxyphenyl)-1-cyclopentyl-N-methoxy-N-methylbenzimidazole-5-carboxamide(Example 34),

[0901]2-(4-benzyloxyphenyl)-1-cyclopentyl-5-(1-hydroxy-1-methylethyl)benzimidazole(Example 35),

[0902] 5-acetyl-2-(4-benzyloxyphenyl)-1-cyclopentylbenzimidazole(Example 36),

[0903]2-(4-benzyloxyphenyl)-1-cyclopentyl-N-(2-dimethylaminoethyl)-benzimidazole-5-carboxamidedihydrochloride (Example 37),

[0904] 2-(4-benzyloxyphenyl)-1-cyclopentyl-5-nitrobenzimidazole (Example38),

[0905] 5-amino-2-(4-benzyloxyphenyl)-1-cyclopentylbenzimidazolehydrochloride (Example 39),

[0906] 5-acetylamino-2-(4-benzyloxyphenyl)-1-cyclopentylbenzimidazole(Example 40),

[0907]2-(4-benzyloxyphenyl)-1-cyclopentyl-5-methanesulfonylaminobenzimidazole(Example 41),

[0908] 5-sulfamoyl-2-(4-benzyloxyphenyl)-1-cyclopentylbenzimidazole(Example 42),

[0909]2-[4-(4-tert-butylbenzyloxy)phenyl]-1-cyclopentylbenzimidazole-5-carboxylicacid (Example 43),

[0910]2-[4-(4-carboxybenzyloxy)phenyl]-1-cyclopentylbenzimidazole-5-carboxylicacid (Example 44),

[0911]2-[4-(4-chlorobenzyloxy)phenyl]-1-cyclopentylbenzimidazole-5-carboxylicacid (Example 45),

[0912]2-{4-[(2-chloro-5-thienyl)methoxy]phenyl}-1-cyclopentylbenzimidazole-5-carboxylicacid (Example 46),

[0913]1-cyclopentyl-2-[4-(4-trifluoromethylbenzyloxy)phenyl]-benzimidazole-5-carboxylicacid (Example 47),

[0914]1-cyclopentyl-2-[4-(4-methoxybenzyloxy)phenyl]benzimidazole-5-carboxylicacid (Example 48),

[0915]1-cyclopentyl-2-[4-(4-pyridylmethoxy)phenyl]benzimidazole-5-carboxylicacid hydrochloride (Example 49),

[0916]1-cyclopentyl-2-[4-(4-methylbenzyloxy)phenyl]benzimidazole-5-carboxylicacid (Example 50),

[0917]1-cyclopentyl-2-{4-[(3,5-dimethyl-4-isoxazolyl)methoxy]phenyl}-benzimidazole-5-carboxylicacid (Example 51),

[0918] 1-cyclopentyl-2-(4-hydroxyphenyl)benzimidazole-5-carboxylic acid(Example 52),

[0919][2-(4-benzyloxyphenyl)-1-cyclopentylbenzimidazol-5-yl]-carbonylaminoaceticacid (Example 53),

[0920]2-[4-(2-chlorobenzyloxy)phenyl]-1-cyclopentylbenzimidazole-5-carboxylicacid (Example 54),

[0921]2-[4-(3-chlorobenzyloxy)phenyl]-1-cyclopentylbenzimidazole-5-carboxylicacid (Example 55),

[0922] 2-(4-benzyloxyphenyl)-3-cyclopentylbenzimidazole-5-carboxylicacid (Example 56),

[0923]2-[4-(benzenesulfonylamino)phenyl]-1-cyclopentylbenzimidazole-5-carboxylicacid (Example 57),

[0924]1-cyclopentyl-2-[4-(3,5-dichlorophenylcarbonylamino)phenyl]-benzimidazole-5-carboxylicacid (Example 58),

[0925]2-{4-[(4-chlorophenyl)carbonylamino]phenyl}-1-cyclopentylbenzimidazole-5-carboxylicacid (Example 59),

[0926]2-{4-[(4-tert-butylphenyl)carbonylamino]phenyl}-1-cyclopentylbenzimidazole-5-carboxylicacid (Example 60),

[0927]2-{4-[(4-benzyloxyphenyl)carbonylamino]phenyl}-1-cyclopentylbenzimidazole-5-carboxylicacid (Example 61),

[0928]trans-4-[2-(4-benzyloxyphenyl)-5-carboxybenzimidazol-1-yl]cyclohexan-1-ol(Example 62),

[0929]trans-1-[2-(4-benzyloxyphenyl)-5-carboxybenzimidazol-1-yl]-4-methoxycyclohexane(Example 63),

[0930] 2-(4-benzyloxyphenyl)-5-carboxymethyl-1-cyclopentylbenzimidazole(Example 64),

[0931]2-[1-benzyloxycarbonyl-4-piperidyl]-1-cyclopentylbenzimidazole-5-carboxylicacid (Example 65),

[0932]22-[(4-cyclohexylphenyl)carbonylamino]-1-cyclopentylbenzimidazole-5-carboxylicacid (Example 66), 5-carboxylic acid (Example 67),

[0933]1-cyclopentyl-2-[4-(3,4-dichlorobenzyloxy)phenyl]benzimidazole-5-carboxylicacid (Example 68),

[0934]1-cyclopentyl-2-[4-(phenylcarbamoylamino)phenyl]benzimidazole-5-carboxylicacid (Example 69),

[0935]1-cyclopentyl-2-[4-(diphenylmethoxy)phenyl]benzimidazole-5-carboxylicacid (Example 70),

[0936] 1-cyclopentyl-2-(4-phenethyloxyphenyl)benzimidazole-5-carboxylicacid (Example 71),

[0937]trans-1-[2-(4-benzyloxyphenyl)-5-carboxybenzimidazol-1-yl]-4-tert-butylcyclohexane(Example 72),

[0938] 2-(4-benzyloxyphenyl)-5-carboxymethoxy-1-cyclopentylbenzimidazole(Example 73),

[0939] 2-(4-benzylaminophenyl)-1-cyclopentylbenzimidazole-5-carboxylicacid (Example 74),

[0940]2-[4-(N-benzenesulfonyl-N-methylamino)phenyl]-1-cyclopentylbenzimidazole-5-carboxylicacid (Example 75),

[0941]2-[4-(N-benzyl-N-methylamino)phenyl]-1-cyclopentylbenzimidazole-5-carboxylicacid (Example 76),

[0942] 1cyclohexyl-2-(4-phenethylphenyl)benzimidazole-5-carboxylic acid(Example 77),

[0943] 2-(1-benzyl-4-piperidyl)-1-cyclopentylbenzimidazole-5-carboxylicacid (Example 78),

[0944] 2-(1-benzoyl-4-piperidyl)-1-cyclopentylbenzimidazole-5-carboxylicacid (Example 79),

[0945]1-cyclopentyl-2-[1-(p-toluenesulfonyl)-4-piperidyl]-benzimidazole-5-carboxylicacid (Example 80),

[0946]1-cyclohexyl-2-[4-(3,5-dichlorobenzyloxy)phenyl]benzimidazole-5-carboxylicacid (Example 81),

[0947]1-cyclohexyl-2-[4-(diphenylmethoxy)phenyl]benzimidazole-5-carboxylicacid (Example 82),

[0948]1-cyclohexyl-2-[4-(3,5-di-tert-butylbenzyloxy)phenyl]-benzimidazole-5-carboxylicacid (Example 83),

[0949]2-(4-benzyloxyphenyl)-1-(4-methylcyclohexyl)benzimidazole-5-carboxylicacid (Example 84),

[0950]1-cyclohexyl-2-{4-[2-(2-naphthyl)ethoxy]phenyl}benzimidazole-5-carboxylicacid (Example 85),

[0951]1-cyclohexyl-2-[4-(1-naphthyl)methoxyphenyl]benzimidazole-5-carboxylicacid (Example 86),

[0952]1-cyclohexyl-2-[4-(dibenzylamino)phenyl]benzimidazole-5-carboxylic acid(Example 87),

[0953]2-[4-(2-biphenylylmethoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 88),

[0954] 2-(4-benzyloxyphenyl)-1-cyclohexylbenzimidazole-5-carboxylic acid(Example 89),

[0955]1-cyclohexyl-2-[4-(dibenzylmethoxy)phenyl]benzimidazole-5-carboxylicacid (Example 90),

[0956] 2-(4-benzoylmethoxyphenyl)-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 91),

[0957] 2-(4-benzyl-1-piperazinyl)-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride (Example 92),

[0958]1-cyclohexyl-2-[4-(3,3-diphenylpropyloxy)phenyl]benzimidazole-5-carboxylicacid (Example 93),

[0959]2-[4-(3-chloro-6-phenylbenzyloxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 94),

[0960] 2-(4-benzyloxypiperidino)-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 95),

[0961]1-cyclohexyl-2-{4-[2-(phenoxy)ethoxy]phenyl}benzimidazole-5-carboxylicacid (Example 96),

[0962]1-cyclohexyl-2-[4-(3-phenylpropyloxy)phenyl]benzimidazole-5-carboxylicacid (Example 97),

[0963]1-cyclohexyl-2-[4-(5-phenylpentyloxy)phenyl]benzimidazole-5-carboxylicacid (Example 98),

[0964]2-(3-benzyloxy-5-isoxazolyl)-1-cyclohexylbenzimidazole-5-carboxylic acid(Example 99),

[0965] 2-(2-benzyloxy-5-pyridyl)-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 100),

[0966] 1-cyclohexyl-2-{4-[2-(3,4,5-trimethoxyphenyl)ethoxy]phenyl}-benzimidazole-5-carboxylic acid(Example 101),

[0967] 2-(4-benzyloxyphenyl)-1-(4,4-dimethylcyclohexyl)benzimidazole-5-carboxylic acid (Example 102),

[0968]1-cyclohexyl-2-{4-[2-(1-naphthyl)ethoxy]phenyl}benzimidazole-5-carboxylicacid (Example 103),

[0969]2-[4-(2-benzyloxyphenoxy)phenyl]-1-cyclohexylbenzimidiazole-5-carboxylicacid (Example 104),

[0970]2-[4-(3-benzyloxyphenoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 105),

[0971]1-cyclohexyl-2-[4-(2-hydroxyphenoxy)phenyl]benzimidazole-5-carboxylicacid (Example 106),

[0972]1-cyclohexyl-2-[4-(3-hydroxyphenoxy)phenyl]benzimidazole-5-carboxylicacid (Example 107),

[0973]1-cyclohexyl-2-[4-(2-methoxyphenoxy)phenyl]benzimidazole-5-carboxylicacid (Example 108),

[0974]1-cyclohexyl-2-[4-(3-methoxyphenoxy)phenyl]benzimidazole-5-carboxylicacid (Example 109),

[0975]1-cyclohexyl-2-[4-(2-propoxyphenoxy)phenyl]benzimidazole-5-carboxylicacid (Example 110),

[0976]1-cyclohexyl-2-[4-(3-propoxyphenoxy)phenyl]benzimidazole-5-carboxylicacid (Example 111),

[0977]1-cyclohexyl-2-{4-[2-(3-methyl-2-butenyloxy)phenoxy]pphenyl}-benzimidazole-5-carboxylicacid (Example 112),

[0978]1-cyclohexyl-2-{4-[3-(3-methyl-2-butenyloxy)phenoxy]phenyl}-benzimidazole-5-carboxylicacid (Example 113),

[0979]1-cyclohexyl-2-[4-(2-isopentyloxyphenoxy)phenyl]benzimidazole-5-carboxylicacid (Example 114),

[0980]1-cyclohexyl-2-[4-(3-isopentyloxyphenoxy)phenyl]benzimidazole-5-carboxylicacid (Example 115),

[0981]1-cyclohexyl-2-{4-[2-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)ethoxy]phenyl}benzimidazole-5-carboxylicacid (Example 116),

[0982]1-cyclohexyl-2-{4-[2-(4-trifluoromethylphenyl)benzyloxy]-phenyl}benzimidazole-5-carboxylicacid (Example 117),

[0983]2-{4-[bis(4-chlorophenyl)methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 118),

[0984]1-cyclohexyl-2-{4-[2-(4-methoxyphenyl)ethoxy]phenyl}-benzimidazole-5-carboxylicacid (Example 119),

[0985]1-cyclohexyl-2-{4-[2-(2-methoxyphenyl)ethoxy]phenyl}-benzimidazole-5-carboxylicacid (Example 120),

[0986]1-cyclohexyl-2-{4-[2-(3-methoxyphenyl)ethoxy]phenyl}-benzimidazole-5-carboxylicacid (Example 121),

[0987] 2-(4-benzyloxyphenyl)-1-cycloheptylbenzimidazole-5-carboxylicacid (Example 122),

[0988]1-cyclohexyl-2-[4-(2-phenethyloxyphenoxy)phenyl]benzimidazole-5-carboxylicacid (Example 123),

[0989]1-cyclohexyl-2-[4-(3-phenethyloxyphenoxy)phenyl]benzimidazole-5-carboxylicacid (Example 124),

[0990]1-cyclohexyl-2-[4-(2,2-diphenylethoxy)phenyl]benzimidazole-5-carboxylicacid (Example 125),

[0991]2-(4-benzyloxyphenyl)-1-(3-cyclohexenyl)benzimidazole-5-carboxylic acid(Example 126),

[0992]cis-1-[2-(4-benzyloxyphenyl)-5-carboxybenzimidazol-1-yl]-4-fluorocyclohexane(Example 127),

[0993]1-cyclohexyl-2-[4-(2-phenoxyphenoxy)phenyl]benzimidazole-5-carboxylicacid (Example 128),

[0994]1-cyclohexyl-2-[4-(3-phenoxyphenoxy)phenyl]benzimidazole-5-carboxylicacid (Example 129),

[0995]2-{4-[(2R)-2-benzyloxycarbonylamino-2-phenylethoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 1301,

[0996]1-cyclohexyl-2-{2-fluoro-4-[2-(4-trifluoromethylphenyl)-benzyloxy]phenyl}benzimidazole-5-carboxylicacid (Example 131),

[0997]2-[4-(4-benzyloxyphenoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 132),

[0998]2-{4-[bis(4-methylphenyl)methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 133),

[0999]2-{4-[bis(4-fluorophenyl)methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 134),

[1000]1-cyclohexyl-6-methoxy-2-[4-(3-phenylpropoxy)phenyl]-benzimidazole-5-carboxylicacid (Example 135),

[1001]1-cyclohexyl-6-hydroxy-2-[4-(3-phenylpropoxy)phenyl]-benzimidazole-5-carboxylicacid (Example 136),

[1002]1-cyclohexyl-6-methyl-2-[4-(3-phenylpropoxy)phenyl]-benzimidazole-5-carboxylicacid (Example 137),

[1003]2-{4-[2-(2-benzyloxyphenyl)ethoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 138),

[1004]2-{4-[2-(3-benzyloxyphenyl)ethoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 139),

[1005]2-[4-(2-carboxymethyloxyphenoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 140),

[1006]2-[4-(3-carboxymethyloxyphenoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 141),

[1007]2-{4-[3-chloro-6-(4-methylphenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 142),

[1008]2-{4-[3-chloro-6-(4-methoxyphenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 143),

[1009]1-cyclohexyl-2-{2-methyl-4-[2-(4-trifluoromethylphenyl)-benzyloxy]phenyl}benzimidazole-5-carboxylicacid (Example 144),

[1010]2-{4-[2-(4-tert-butylphenyl)-5-chlorobenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 145),

[1011]2-{4-(3-chloro-6-phenylbenzyloxy)-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 146),

[1012]2-{4-[3-chloro-6-(3,5-dichlorophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 147),

[1013]2-{4-[bis(4-fluorophenyl)methoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 148),

[1014]2-{4-(4-benzyloxyphenoxy)-2-chlorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 149),

[1015]2-{4-(4-benzyloxyphenoxy)-2-trifluoromethylphenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 150),

[1016]2-{4-[3-chloro-6-(2-trifluoromethylphenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 1511,

[1017]2-{4-[(2R)-2-amino-2-phenylethoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 1521,

[1018]2-[4-(2-biphenylyloxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 153),

[1019]2-[4-(3-biphenylyloxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 154),

[1020] 2-{4-[2-{(1-tert-butoxycarbonyl-4-piperidyl)methoxyphenoxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylic acid (Example155),

[1021] 2-{4-[3-1(1-tert-butoxycarbonyl-4-piperidyl)methoxy}phenoxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 156),

[1022]2-{4-[3-chloro-6-(3,4,5-trimethoxyphenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 157),

[1023]2-{4-[2-(2-biphenylyl)ethoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 158),

[1024]2-[4-(2-biphenylylmethoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 159),

[1025]1-cyclohexyl-2-{4-[2-(4-piperidylmethoxy)phenoxy]phenyl}-benzimidazole-5-carboxylicacid hydrochloride (Example 160),

[1026]1-cyclohexyl-2-{4-[3-(4-piperidylmethoxy)phenoxy]phenyl}-benzimidazole-5-carboxylicacid hydrochloride (Example 161),

[1027]2-{4-[(2R)-2-acetylamino-2-phenylethoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 162),

[1028]1-cyclohexyl-2-{4-[3-(4-methyl-3-pentenyloxy)phenoxy]phenyl}-benzimidazole-5-carboxylicacid (Example 163),

[1029]1-cyclohexyl-2-{4-[3-(3-methyl-3-butenyloxy)phenoxy]phenyl}-benzimidazole-5-carboxylicacid (Example 164),

[1030]2-{4-[{(2S)-1-benzyl-2-pyrrolidinyl}methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 165)

[1031]2-{4-[3-chloro-6-(4-methylthiophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 166),

[1032]2-{4-[3-chloro-6-(4-methanesulfonylphenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 167),

[1033]2-{4-[3-chloro-6-(2-thienyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 168),

[1034]2-{4-[3-chloro-6-(3-chlorophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 169),

[1035]2-{4-[3-chloro-6-(3-pyridyl)benzyloxy]phenyl}7-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 170),

[1036]2-{4-[3-chloro-6-(4-fluorophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 171),

[1037]2-[4-(4-benzyloxyphenoxy)-3-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 172),

[1038]2-[4-(2-bromo-5-chlorobenzyloxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 173),

[1039]2-{4-[3-chloro-6-(4-chlorophenyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 174),

[1040]2-{4-[2-{(1-acetyl-4-piperidyl)methoxy}phenoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 175),

[1041]2-{4-[3-{(1-acetyl-4-piperidyl)methoxy}phenoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 176),

[1042]1-cyclohexyl-2-{4-[3-(2-propynyloxy)phenoxy]phenyl}benzimidazole-5-carboxylicacid (Example 177),

[1043]1-cyclohexyl-2-{4-[3-(3-pyridylmethoxy)phenoxy]phenyl}-benzimidazole-5-carboxylicacid (Example 178),

[1044]2-(4-benzyloxy-2-methoxyphenyl)-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 179),

[1045]2-[4-(2-bromo-5-methoxybenzyloxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 180),

[1046]2-[4-(carboxydiphenylmethoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 181),

[1047]2-{4-[2-(4-chlorophenyl)-5-nitrobenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 182),

[1048]2-{4-[3-acetylamino-6-(4-chlorophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 183),

[1049]2-{4-[2-(4-carboxyphenyl)-5-chlorobenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 184),

[1050]2-{4-[{(2S)-1-benzyloxycarbonyl-2-pyrrolidinyl}methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 185),

[1051]2-{2-chloro-4-[2-(4-trifluoromethylphenyl)benzyloxy]phlenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 186),

[1052]1-cyclohexyl-2-{4-[3-(2-pyridylmethoxy)phenoxy]phenyl}-benzimidazole-5-carboxylicacid (Example 187),

[1053]2-{4-[2-(4-chlorophenyl)-5-fluorobenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 188),

[1054]2-{4-[3-carboxy-6-(4-chlorophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 189),

[1055]2-{4-[3-carbamoyl-6-(4-chlorophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 190),

[1056]1-cyclohexyl-2-{4-[2-(dimethylcarbamoylmethoxy)phenoxy]-phenyl}benzimidazole-5-carboxylicacid (Example 191),

[1057]1-cyclohexyl-2-{4-[2-(piperidinocarbonylmethoxy)phenoxy]-phenyl}benzimidazole-5-carboxylicacid (Example 192),

[1058]2-{4-[{(2S)-1-benzenesulfonyl-2-pyrrolidinyl}methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 193),

[1059]2-{4-[{(2S)-1-benzoyl-2-pyrrolidinyl}methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 194),

[1060]2-{4-[2-(4-carbamoylphenyl)-5-chlorobenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 195),

[1061]1-cyclohexyl-2-{4-[3-(dimethylcarbamoylmethoxy)phenoxy]-phenyl}benzimidazole-5-carboxylicacid (Example 196),

[1062]1-cyclohexyl-2-{4-[3-(piperidinocarbonylmethoxy)phenol]-phenyl}benzimidazole-5-carboxylicacid (Example 197),

[1063]1-cyclohexyl-2-{4-[3-{(1-methanesulfonyl-4-piperidyl)methoxy}-phenoxy]phenyl}benzimidazole-5-carboxylicacid (Example 198),

[1064]1-cyclohexyl-2-{4-[{2-methyl-5-(4-chlorophenyl)-4-oxazolyl}-methoxy]phenyl}benzimidazole-5-carboxylicacid (Example 199),

[1065]2-{4-[3-(3-chlorobenzyloxy)phenoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 200),

[1066]2-{4-[3-(4-chlorobenzyloxy)phenoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 201),

[1067]1-cyclohexyl-2-{4-[3-(4-fluorobenzyloxy)phenoxy]pheny}-benzimidazole-5-carboxylicacid (Example 202),

[1068]1-cyclohexyl-2-{4-[{(2S)-1-(4-nitrophenyl)-2-pyrrolidinyl}-methoxy]phenyl}benzimidazole-5-carboxylicacid (Example 203),

[1069]1-cyclohexyl-2-{4-[{(2S)-1-phenyl-2-pyrrolidinyl}methoxy]-phenyl}benzimidazole-5-carboxylicacid hydrochloride (Example 204),

[1070]2-{4-[{(2S)-1-(4-acetylaminophenyl)-2-pyrrolidinyl}methoxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 205),

[1071]2-{4-[{5-(4-chlorophenyl)-2-methyl-4-thiazoly}methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 206),

[1072]2-{4-[bis(3-fluorophenyl)methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 207),

[1073]1-cyclohexyl-2-{4-[2-(4-chlorophenyl)-3-nitrobenzyloxy]phenyl}-benzimidazole-5-carboxylicacid (Example 208),

[1074]1-cyclohexyl-2-{4-[3-(4-tetrahydropyranyloxy)phenoxy]phenyl}-benzimidazole-5-carboxylicacid (Example 209),

[1075]1-cyclohexyl-2-{4-[3-(4-trifluoromethylbenzyloxy)phenoxy]phenyl}-benzimidazole-5-carboxylicacid (Example 210),

[1076]1-cyclohexyl-2-{4-[3-{(1-methyl-4-piperidyl)methoxy}phenoxy]-phenyl}benzimidazole-5-carboxylicacid (Example 211),

[1077]2-{4-[3-(4-tert-butylbenzyloxy)phenoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 212),

[1078]2-{4-[3-(2-chlorobenzyloxy)phenoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 213),

[1079]1-cyclohexyl-2-{4-[3-(3-pyridyl)phenoxy]phenyl}benzimidazole-5-carboxylicacid (Example 214),

[1080]2-{4-[3-(4-chlorophenyl)phenoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 215),

[1081]1-cyclohexyl-2-{4-[3-(4-methoxyphenyl)phenoxy]phenyl}-benzimidazole-5-carboxylicacid (Example 216),

[1082]1-cyclohexyl-2-{4-[4-(4-methanesulfonylphenyl)-2-methyl-5-thiazolylmethoxy]phenyl}benzimidazole-5-carboxylic acid (Example 217),

[1083]2-{4-[{4-(4-chlorophenyl)-2-methyl-5-thiazolyl}ethoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 218),

[1084]2-{4-[1-(4-chlorobenzyl)-3-piperidyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 219),

[1085]1-cyclohexyl-2-{4-[3-{(2-methyl-4-thiazolyl)methoxy}phenoxy]-phenyl}benzimidazole-5-carboxylicacid (Example 220),

[1086]1-cyclohexyl-2-{4-[3-{(2,4-dimethyl-5-thiazolyl)methoxy}phenoxy]-phenyl}benzimidazole-5-carboxylicacid (Example 221),

[1087]1-cyclohexyl-2-{4-[3-(3,5-dichlorophenyl)phenoxy]phenyl}-benzimidazole-5-carboxylicacid (Example 222),

[1088]2-{4-[1-(4-chlorobenzyl)-4-piperidyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 223),

[1089]2-{4-[3-(4-chlorobenzyloxy)piperidino]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 224),

[1090]2-{4-[4-carbamoyl-2-(4-chlorophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 225),

[1091]2-{4-[4-(4-chlorobenzyloxy)piperidino]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 226),

[1092]2-{4-[3-{(2-chloro-4-pyridyl)methoxy}phenoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 227),

[1093]2-{4-[{(2S)-1-(4-dimethylcarbamoylphenyl)-2-pyrrolidinyl}-methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 228),

[1094]2-{4-[2-(4-chlorophenyl)-5-ethoxycarbonylbenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 229),

[1095]1-cyclohexyl-2-[4-(3-trifluoromethylphenoxy)phenyl]-benzimidazole-5-carboxylicacid (Example 230),

[1096]1-cyclohexyl-2-{4-[{4-(4-dimethylcarbamoylphenyl)-2-methyl-5-thiazolyl}methoxy]phenyl}benzimidazole-5-carboxylicacid (Example 231),

[1097]2-{4-[2-(4-chlorophenyl)-5-dimethylcarbamoylbenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 232),

[1098]2-{4-[{4-(4-chlorophenyl)-2-methyl-5-pyrimidinyl}methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 233),

[1099]2-{4-[{2-(4-chlorophenyl)-3-pyridyl}methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride (Example 234),

[1100]2-{4-[{3-(4-chlorophenyl)-2-pyridyl}methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 235),

[1101]2-{4-[2-(3-chlorophenyl)-4-methylamino-1,3,5-triazin-6-yloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid trifluoroacetate (Example 236),

[1102]2-{4-[2-(4-chlorophenyl)-4-(5-tetrazolyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 237),

[1103]2-[4-(4-benzyloxy-6-pyrimidinyloxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 238),

[1104]1-cyclohexyl-2-{4-[4-(4-pyridylmethoxy)-6-pyrimidinyloxy]phenyl}-benzimidazole-5-carboxylicacid (Example 239),

[1105]2-{4-[4-(3-chlorophenyl)-6-pyrimidinyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 2401,

[1106] methyl2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylate(Example 241),

[1107]2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 242),

[1108] ethyl2-{4-[3-(4-chlorophenyl)pyridin-2-ylmethoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylate(Example 243),

[1109] methyl2-[4-(2-bromo-5-tert-butoxycarbonylbenzyloxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylate(Example 244),

[1110] methyl2-{4-[5-tert-butoxycarbonyl-2-(4-chlorophenyl)benzyloxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylate(Example 245),

[1111] methyl2-{4-[5-carboxy-2-(4-chlorophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylatehydrochloride (Example 246),

[1112] methyl2-{4-[2-(4-chlorophenyl)-5-methylcarbamoylbenzyloxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylate(Example 247),

[1113]2-{4-[2-(4-chlorophenyl)-5-methylcarbamoylbenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 248),

[1114]2-{4-[3-(tert-butylsulfamoyl)-6-(4-chlorophenyl)benzyloxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 249),

[1115]2-{4-[2-(4-chlorophenyl)-5-sulfamoylbenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid trifluoroacetate (Example 250),

[1116] 2-(4-benzyloxycyclohexyl)-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 251),

[1117]2-[2-(2-biphenylyloxymethyl)-5-thienyl]-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 252),

[1118]2-[2-(2-biphenylyloxymethyl)-5-furyl]-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 253),

[1119]1-cyclohexyl-2-{4-[{4-(4-fluorophenyl)-2-hydroxymethyl-5-thiazolyl}methoxy]phenyl}benzimidazole-5-carboxylicacid (Example 254),

[1120]1-cyclohexyl-2-{4-[{4-(4-carboxyphenyl)-2-methyl-5-thiazolyl}-methoxy]phenyl}benzimidazole-5-carboxylicacid hydrochloride (Example 255),

[1121]1-cyclohexyl-2-{2-fluoro-4-[4-fluoro-2-(3-fluorobenzoyl)-benzyloxy]phenyl}benzimidazole-5-carboxylicacid (Example 256),

[1122]2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-sulfonicacid (Example 257),

[1123]2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-3-cyclohexylbenzimidazole-4-carboxylicacid (Example 258),

[1124]1-cyclohexyl-2-{4-[3-dimethylcarbamoyl-5-(4-pyridylmethoxy)-phenoxy]phenyl}benzimidazole-5-carboxylicacid dihydrochloride (Example 259),

[1125]1-cyclohexyl-2-{4-[3-carboxy-5-(4-pyridylmethoxy)phenoxy]-phenyl}benzimidazole-5-carboxylicacid dihydrochloride (Example 260),

[1126]2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-1-cyclohexylbenzimidazole-4-carboxylicacid (Example 261),

[1127]2-{4-[3-carbamoyl-6-(4-chlorophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 262),

[1128]2-{4-[{2-(4-carboxyphenyl)-3-pyridyl}methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 263),

[1129]2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-1-(4-tetrahydrothiopyranyl)benzimidazole-5-carboxylicacid (Example 264),

[1130]2-{4-[2-(4-chlorophenyl)-5-dimethylcarbamoylbenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 265),

[1131]1-cyclohexyl-2-{4-[3-dimethylcarbamoyl-6-(4-trifluoromethylphenyl)benzyloxy]phenyl}benzimidazole-5-carboxylicacid hydrochloride (Example 266),

[1132]1-cyclohexyl-2-{4-[3-dimethylcarbamoyl-6-(4-methylthiophenyl)-benzyloxy]phenyl}benzimidazole-5-carboxylicacid hydrochloride (Example 267),

[1133]2-{4-[2-(4-chlorophenyl)-5-methylcarbamoylbenzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 268),

[1134]2-{4-[2-(4-chlorophenyl)-5-dimethylcarbamoylbenzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 269),

[1135]2-{4-[3-carbamoyl-6-(4-chlorophenyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 270),

[1136]2-{4-[3-dimethylcarbamoyl-6-(4-methanesulfonylphenyl)ibenzyloxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 271),

[1137]2-{4-[3-dimethylcarbamoyl-6-(3-pyridyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride (Example 272),

[1138]2-{4-[3-dimethylcarbamoyl-6-(4-dimethylcarbamoylphenyl)-benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 273),

[1139]2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-1-(1-oxo-4-tetrahydrothiopyranyl)benzimidazole-5-carboxylicacid (Example 274),

[1140]2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-1-(1,1-dioxo-4-tetrahydrothiopyranyl)benzimidazole-5-carboxylicacid (Example 275),

[1141]2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]-2-fluorophenyl}-1-(4-tetrahydrothiopyranyl)benzimidazole-5-carboxylicacid (Example 276),

[1142]2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]-2-fluorophenyl}-1-(1-oxo-4-tetrahydrothiopyranyl)benzimidazole-5-carboxylicacid (Example 277),

[1143]2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]-2-fluorophenyl}-1-(1,1-dioxo-4-tetrahydrothiopyranyl)benzimidazole-5-carboxylicacid (Example 278),

[1144]2-{4-[2-(4-chlorophenyl)-5-dimethylsulfamoylbenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 279),

[1145]2-{4-[2-(4-chlorophenyl)-5-methanesulfonylbenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 280),

[1146] methyl2-{4-[5-carboxy-2-(4-chlorophenyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylatehydrochloride (Example 281),

[1147]2-{4-[2-(4-chlorophenyl)-5-dimethylaminobenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride (Example 282),

[1148]2-{4-[2-(4-chlorophenyl)-5-methanesulfonylaminobenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 283),

[1149]2-{4-[2-(4-chlorophenyl)-5-diethylcarbamoylbenzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 284),

[1150]2-{4-[2-(4-chlorophenyl)-5-isopropylcarbamoylbenzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 285),

[1151]2-{4-[2-(4-chlorophenyl)-5-piperidinocarbonylbenzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 286),

[1152]2-{4-[2-(4-chlorophenyl)-5-(1-pyrrolidinyl)carbonylbenzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 287),

[1153]2-{4-[2-(4-chlorophenyl)-5-(2-hydroxyethyl)carbamoylbenzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 288),

[1154]2-{4-[2-(4-chlorophenyl)-5-(4-hydroxypiperidino)-carbonylbenzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 289),

[1155]2-{4-[2-(4-chlorophenyl)-5-morpholinocarbonylbenzyloxyr]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 290),

[1156]2-{4-[2-(4-chlorophenyl)-5-thiomorpholinocarbonylbenzyrloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 291),

[1157]2-{4-[3-(carboxymethylcarbamoyl)-6-(4-chlorophenyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 292),

[1158]2-{4-[2-{4-(2-carboxyethyl)phenyl}-5-chlorobenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 293),

[1159]2-{4-[3-chloro-6-(4-hydroxymethylphenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 294),

[1160]2-{4-[3-chloro-6-(4-methoxymethylphenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 295),

[1161]2-{4-[2-(3-carboxyphenyl)-5-chlorobenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 296),

[1162]2-{4-[2-(4-chlorophenyl)-5-methylthiobenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 297),

[1163]2-{4-[2-(4-chlorophenyl)-5-methylsulfinylbenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 298),

[1164]2-{4-[2-(4-chlorophenyl)-5-cyanobenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 299),

[1165]2-{4-[bis(3-pyridyl)methoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 300),

[1166]2-{4-[bis(4-dimethylcarbamoylphenyl)methoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 301),

[1167] sodium2-{4-[2-thienyl-3-thienylmethoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylate(Example 302),

[1168] methyl2-{4-[2-(4-chlorophenyl)-5-(dimethylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylate(Example 303),

[1169] sodium2-{4-[2-(4-chlorophenyl)-5-(dimethylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylate(Example 304),

[1170]2-{4-[5-carboxy-2-(4-chlorophenyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 305),

[1171]2-{4-[2-(4-carboxyphenyl)-5-methoxybenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 306),

[1172]2-{4-[2-(4-carbamoylphenyl)-5-(dimethylcarbamoyl)benzyloxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 307),

[1173]2-{4-[5-amino-2-(4-chlorophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 308),

[1174]2-{4-[5-(4-chlorophenyl)-2-methoxybenzylsulfinyl]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 309),

[1175]2-{4-[5-(4-chlorophenyl)-2-methoxybenzylsulfonyl]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 310),

[1176]2-{4-[2-(4-chlorophenyl)-5-methoxybenzylthio]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 311),

[1177]2-{4-[bis(4-carboxyphenyl)methoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 312),

[1178]2-[4-(phenyl-3-pyridylmethoxy)-2-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 313),

[1179] methyl2-{4-[2-(4-chlorophenyl)-5-(methylcarbamoyl)berizyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylate(Example 314),

[1180]2-{4-[5-chloro-2-(4-pyridyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 315),

[1181]2-{4-[2-(4-chlorophenyl)-5-(benzylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 316),

[1182]2-{4-[2-(4-chlorophenyl)-5-(cyclohexylmethylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 317),

[1183]2-{4-[2-(4-chlorophenyl)-5-(4-pyridylmethylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride (Example 318),

[1184]2-{4-[2-(4-chlorophenyl)-5-(N-benzyl-N-methylcarbamoyl)-benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 319),

[1185] methyl2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-1-cyclohexyl-1H-indole-5-carboxylate(Example 501),

[1186]2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-1-cyclohexyl-1H-indole-5-carboxylicacid (Example 502),

[1187] 2-(4-benzyloxyphenyl)-1-cyclopentyl-1H-indole-5-carboxylic acid(Example 503),

[1188] ethyl2-(4-benzyloxyphenyl)-3-cyclohexylimidazo[1,2-a]pyridine-7-carboxylate(Example 601),

[1189]2-(4-benzyloxyphenyl)-3-cyclohexylimidazo[1,2-a]pyridine-7-carboxylicacid (Example 602), and

[1190]2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-3-cyclohexyl-3H-imidazo[4,5-b]pyridine-6-carboxylicacid (Example 701).

[1191] (92) The fused ring compound of the formula [I] or apharmaceutically acceptable salt thereof, which is selected from thegroup consisting of

[1192]2-{4-[5-dimethylaminocarbonyl-2-(4-pyridyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride (Example 320),

[1193]2-{4-[2-(4-chlorophenyl)-5-(4-methylpiperazin-1-ylcarbonyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride (Example 321),

[1194]2-{4-[2-(4-chlorophenyl)-5-{N-(3-pyridylmethyl)carbamoyl}-benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride (Example 322),

[1195]2-{4-[2-(4-chlorophenyl)-5-{N-(2-pyridylmethyl)carbamoyl}-benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride (Example 323),

[1196]2-{4-[2-(4-chlorophenyl)-5-(cyclohexylcarbamoyl)benzyloxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 324),

[1197]2-{4-[2-(4-chlorophenyl)-5-(2-pyridin-4-ylethylcarbamoyl)-benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride (Example 325),

[1198]2-{4-[(4-fluorophenyl){4-(dimethylaminocarbonyl)phenyl}methoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 326),

[1199]2-{4-[(4-fluorophenyl)(4-carboxyphenyl)methoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 327),

[1200]2-{4-[2-(4-chlorophenyl)-5-(4-oxopiperidinocarbonyl)-benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 328),

[1201]2-{4-[2-(4-chlorophenyl)-5-hydroxybenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 329),

[1202]2-{4-[2-(4-chlorophenyl)-5-(isopropylcarbamoyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 330),

[1203]2-{4-[2-(4-chlorophenyl)-5-(N-isopropyl-N-methylcarbamoyl)-benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 331),

[1204]2-{4-[2-(4-chlorophenyl)-5-(phenylcarbamoyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 332),

[1205]2-{4-[2-(4-chlorophenyl)-5-(4-methoxypiperidinocarbonyl)-benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 333),

[1206]2-{4-[2-(4-chlorophenyl)-5-(3-hydroxypropyloxy)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 334), and

[1207]2-{4-[2-(4-chlorophenyl)-5-(2-hydroxyethoxy)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 335).

[1208] (93) The fused ring compound of the formula [I] or apharmaceutically acceptable salt thereof, which is selected from thegroup consisting of

[1209] methyl2-[4-(2-bromo-5-nitrobenzyloxy)-2-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylate(Example 336),

[1210] methyl2-[4-{2-(4-chlorophenyl)-5-nitrobenzyloxy}-2-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylate(Example 337),

[1211] methyl2-[4-{5-amino-2-(4-chlorophenyl)benzyloxy}-2-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylate(Example 338),

[1212] methyl2-[4-{2-(4-chlorophenyl)-5-(2-oxopyrrolidin-1-yl)benzyloxy}-2-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylate(Example 339),

[1213]2-[4-{2-(4-chlorophenyl)-5-(2-oxopyrrolidin-1-yl)benzyloxy}-2-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 340),

[1214]2-{4-[2-(4-chlorophenyl)-5-(4-methylpiperidin-1-ylcarbonyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 341),

[1215]2-{4-[5-acetyl-2-(4-chlorophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 342),

[1216]2-{4-[2-(4-chlorophenyl)-5-{(4-hydroxypiperidin-1-ylcarbonyl)-methoxy}benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 343),

[1217]2-{4-[2-(4-chlorophenyl)-5-(2-methoxyethoxy)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 344),

[1218]2-{4-[2-(4-chlorophenyl)-5-{2-(2-methoxyethoxy)ethoxy}-benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 345),

[1219]2-{4-[2-(4-chlorophenyl)-5-(isobutylcarbonyl)benzyloxyr]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 346),

[1220]2-{4-[2-(4-chlorophenyl)-5-(2-methylthiazol-4-yl)benzyrloxy]-phenyl}-cyclohexylbenzimidazole-5-carboxylicacid (Example 347),

[1221]2-{4-[2-(4-chlorophenyl)-5-(3,4-dihydroxypiperidin-1-ylcarbonyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 348),

[1222]2-{4-[2-(4-chlorophenyl)-5-(3-methyl-1,2,4-oxadiazole)-yl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 349),

[1223]2-{4-[2-(4-chlorophenyl)-4-((isopropylcarbamoyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 350),

[1224]2-{4-[2-(4-chlorophenyl)-4-(piperidinocarbonyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 351),

[1225]2-{4-[2-(4-chlorophenyl)-5-{(1-hydroxy-2-methylpropan-2-yl)carbamoylbenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylic acidhydrochloride (Example 352),

[1226]2-{4-[2-(4-chlorophenyl)-5-(4,4-dimethyl-2-oxazolin-2-yl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride (Example 353),

[1227]2-4-[2-(4-chlorophenyl)-4-(4-hydroxypiperidin-1-ylcarbonyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 354),

[1228]2-{4-[2-(4-chlorophenyl)-4-{(2-hydroxyethyl)carbamoyl}-benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 355),

[1229]2-{4-[2-(4-chlorophenyl)-4-{(4-pyridylmethyl)carbamoyl}-benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 356),

[1230]2-{4-[2-(4-chlorophenyl)-4-(dimethylcarbamoyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 357),

[1231]2-{4-[5-(2-aminothiazol-4-yl)-2-(4-chlorophenyl)benzyloxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride (Example 358),

[1232]2-{4-[2-(4-chlorophenyl)-5-(4-hydroxypiperidin-1-ylsulfonyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 359),

[1233]2-{4-[5-(dimethylcarbamoyl)-2-(4-fluorophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 360),

[1234]2-{4-[5-(dimethylcarbamoyl)-2-(3-fluorophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 361),

[1235]2-{4-[2-(5-chlorothiophen-2-yl)-5-(dimethylcarbamoyl)benzyloxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 362),

[1236]2-{4-[2-bromo-5-(5-methyloxazol-2-yl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 363)

[1237]2-{4-[2-bromo-5-(5-methylthiazol-2-yl)benzyloxy]pheny}7-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 364),

[1238]2-{4-[2-(4-chlorophenyl)-5-(5-methyloxazol-2-yl)benzyloxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 365),

[1239]2-{4-[2-(4-chlorophenyl)-5-(5-methylthiazol-2-yl)benzyloxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 366),

[1240]2-{4-[2-(4-chlorophenyl)-5-tetrazol-5-ylbenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 367),

[1241]2-{4-[5-chloro-2-(4-cyanophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 368),

[1242]2-{4-[5-chloro-2-(4-tetrazol-5-ylphenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 369),

[1243] 2-{4-[2-(4-chlorophenyl)-5-{2-(4-hydroxypiperidin-1-yl)ethoxy}benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylic acidhydrochloride (Example 370),

[1244]2-{4-[2-(4-chlorophenyl)-5-(2-oxopiperidin-1-yl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 371),

[1245]2-{4-[3-(4-chlorophenyl)-5-(dimethylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 372),

[1246]2-{4-[2-(4-chlorophenyl)-5-(N-hydroxyamidino)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride (Example 373),

[1247]2-{4-[2-(4-chlorophenyl)-5-(2,5-dihydro-5-oxo-4H-1,2,4-oxadiazol-3-yl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 374),

[1248]2-{4-[2-(4-chlorophenyl)-5-(2-oxo-3H-1,2,3,5-oxathiadimazol-4-yl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 375),

[1249]2-{4-[2-(4-chlorophenyl)-5-(2,5-dihydro-5-oxo-4H-1,2,4-thiadiazol-3-yl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 376),

[1250]2-{4-[2-(4-chlorophenyl)-5-(cyclopropylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 377),

[1251]2-{4-[2-(4-chlorophenyl)-5-(cyclobutylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 378),

[1252]2-{4-[2-(4-chlorophenyl)-5-(tert-butylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 379),

[1253]2-{4-[2-(4-chlorophenyl)-5-(isobutylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 380),

[1254]2-{4-[2-(4-chlorophenyl)-5-{(1-hydroxypropan-2-yl)carbamoyl}-benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 381),

[1255]2-{4-[2-(4-chlorophenyl)-5-(methoxycarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 382),

[1256]2-{4-[2-(4-chlorophenyl)-5-{(2,3-dihydroxypropyl)carbemoyl}-benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 383),

[1257]2-{4-[2-(4-chlorophenyl)-5-(N-ethyl-N-methylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 384),

[1258]2-{4-[2-(4-chlorophenyl)-5-(N-methyl-N-propylcarbamoyl)-benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 385),

[1259]2-{4-[2-(4-chlorophenyl)-5-(N-isopropyl-N-methylcarbanoyl)-benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 386),

[1260]2-{4-[2-(4-chlorophenyl)-5-(2,6-dimethylpiperidin-1-ylcarbonyl)-benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 387),

[1261]2-{4-[5-(butylcarbamoyl)-2-(4-chlorophenyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 388),

[1262]2-{4-[2-(4-chlorophenyl)-5-(propylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicac-id hydrochloride (Example 389),

[1263]2-{4-[2-(4-chlorophenyl)-5-(ethylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 390),

[1264]2-{4-[2-(4-chlorophenyl)-5-{(dimethylcarbamoyl)amino}benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 391),

[1265]2-{4-[2-(4-chlorophenyl)-5-{(morpholinocarbonyl)amino}benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 392),

[1266]2-{4-[2-(4-chlorophenyl)-5-ureidobenzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 393),

[1267] 2-{4-[2-(4-chlorophenyl)-5-{(ethylcarbamoyl)aminobenzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylic acidhydrochloride (Example 394),

[1268] 2-{4-[2-(4-chlorophenyl)-5-{(isopropylcarbamoyl)amino}benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 395),

[1269]2-{4-[2-(3,4-difluorophenyl)-5-(isopropylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 396),

[1270]2-{4-[2-(2,4-difluorophenyl)-5-(isopropylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 397),

[1271]2-{4-[2-(3,5-dichlorophenyl)-5-(isopropylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 398),

[1272]2-{4-[2-(3-chloro-4-fluorophenyl)-5-(isopropylcarbamoyl)-benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 399),

[1273]2-{4-[2-(3,4-dichlorophenyl)-5-(isopropylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 400),

[1274]2-{4-[2-(4-chloro-2-fluorophenyl)-5-(isopropylcarbamoyl)-benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 401),

[1275]2-{4-[2-(4-chloro-2-fluorophenyl)-5-(pyrrolidin-1-ylcarbonyl)-benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 402),

[1276]2-{4-[2-(4-chloro-3-fluorophenyl)-5-(pyrrolidin-1-ylcarbonyl)-benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 403),

[1277]2-{4-[2-(4-chloro-3-fluorophenyl)-5-(isopropylcarbamoyl)-benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 404),

[1278]2-{4-[2-{4-(methylthio)phenyl}-5-(2-oxopyrrolidin-1-yl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 405),

[1279]2-{4-[2-{4-(methylthio)phenyl}-5-(isopropylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 406),

[1280]2-{4-[4-chloro-2-(4-chlorophenyl)-5-(1,1-dioxoisothiazolidin-2-yl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazol(s-5-carboxylicacid hydrochloride (Example 407),

[1281]2-{4-[4-chloro-2-(4-chlorophenyl)-5-(2-oxopyrrolidin-1-yl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 408),

[1282]2-{4-[2-(4-chlorophenyl)-5-(isopropylaminosulfonyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 409),

[1283]2-{4-[2-(4-chlorophenyl)-5-(dimethylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclopentylbenzimidazole-5-carboxylicacid hydrochloride (Example 410),

[1284]2-{4-[2-(4-chlorophenyl)-5-(4-hydroxypiperidin-1-ylcarbonyl)-benzyloxy]-2-fluorophenyl}-1-cyclopentylbenzimidazole-5-carboxylicacid hydrochloride (Example 411),

[1285]2-{4-[2-(4-chlorophenyl)-5-(isopropylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclopentylbenzimidazole-5-carboxylicacid hydrochloride (Example 412),

[1286]2-{4-[2-(4-chlorophenyl)-5-(isopropylcarbamoyl)benzyloxy]phenyl}-1-cyclopentylbenzimidazole-5-carboxylicacid hydrochloride (Example 413)

[1287]2-{4-[2-(4-chlorophenyl)-5-(dimethylcarbamoyl)benzyloxyphenyl}-1-cyclopentylbenzimidazole-5-carboxylicacid hydrochloride (Example 414)

[1288]2-{4-[2-(4-chlorophenyl)-5-(4-hydroxypiperidin-1-ylcarbonyl)benzyloxy]phenyl}-1-cyclopentylbenzimidazole-5-carboxylicacid hydrochloride (Example 415),

[1289]2-{4-[2-(4-chlorophenyl)-5-(isopropylcarbamoyl)benzyloxy]phenyl}-1-(tetrahydrothiopyran-4-yl)benzimidazole-5-carboxylicacid hydrochloride (Example 416),

[1290]2-{4-[2-(4-chlorophenyl)-5-(pyrrolidin-1-ylcarbonyl)benzyloxy]-phenyl}-1-(tetrahydrothiopyran-4-yl)benzimidazole-5-carboxylicacid hydrochloride (Example 417),

[1291]2-{4-[2-(4-chlorophenyl)-5-(isopropylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-(tetrahydrothiopyran-4-yl)benzimidazole-5-carboxylicacid hydrochloride (Example 418),

[1292]2-{4-[2-(4-chlorophenyl)-5-(2-oxopyrrolidin-1-yl)benzyrloxy]-2-fluorophenyl}-1-(tetrahydrothiopyran-4-yl)benzimidazole-5-carboxylicacid hydrochloride (Example 419),

[1293]2-{4-[2-(4-chlorophenyl)-5-(isopropylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-piperidinobenzimidazole-5-carboxylicacid hydrochloride (Example 420),

[1294]2-{4-[2-(4-chlorophenyl)-5-(pyrrolidin-1-ylcarbonyl)benzyloxy]-2-fluorophenyl}-1-piperidinobenzimidazole-5-carboxylicacid (Example 421),

[1295]2-{4-[2-(4-chlorophenyl)-5-(2-imidazolin-2-yl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride (Example 422),

[1296]2-{4-[2-(4-chlorophenyl)-5-(2-oxooxazolidin-3-yl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 423),

[1297]2-{4-[2-(4-chlorophenyl)-5-(2-oxoimidazolidin-1-yl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 424),

[1298]2-{4-[2-(4-chlorophenyl)-5-(2-oxazolin-2-ylamino)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride (Example 425),

[1299]2-{4-[{2-[{(dimethylcarbamoyl)methoxy}methyl]-4-(4-fluorophenyl)thiazol-5-yl}ethoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 426),

[1300]2-{4-{4-(4-fluorophenyl)-2-(4-hydroxypiperidin-1-ylmethyl)thiazol-5-yl}methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride (Example 427),

[1301]2-{4-[{4-(4-fluorophenyl)-2-[(carbamoylmethoxy)methyl]thiazol-5-yl}ethoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 428),

[1302]2-{4-[{4-(4-fluorophenyl)-2-(methylcarbamoyl)thiazol-5-yl}ethoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 429),

[1303]2-{4-[{4-(4-fluorophenyl)-2-{(2-hydroxyethyl)carbamoyl}thiazol-5-yl}methoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole)-carboxylicacid hydrochloride (Example 430),

[1304]2-{4-[{2-(4-fluorophenyl)-5-(dimethylcarbamoyl)thiophen-3-yl}methoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5)-carboxylicacid hydrochloride (Example 431),

[1305]2-{4-[{2-(4-fluorophenyl)-5-(isopropylcarbamoyl)thiophen-3-yl}ethoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 432),

[1306]2-{4-[{2-(4-fluorophenyl)-5-(4-hydroxypiperidin-1-ylcarbonyl)thiophen-3-yl}methoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 433),

[1307]2-{4-[2-(4-chlorophenyl)-5-(dimethylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexyl-5-tetrazol-5-ylbenzimidazole(Example 434),

[1308]2-{4-[2-(4-carboxyphenyl)-5-chlorobenzyloxy]-2-fluorophenyl}-1-cyclohexyl-5-tetrazol-5-ylbenzimidazolehydrochloride (Example 435),

[1309]2-{4-[2-(4-chlorophenyl)-5-(isopropylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexyl-5-(2,5-dihydro-5-oxo-4H-1,2,4-oxadiazol-3-yl)benzimidazolehydrochloride (Example 436),

[1310]2-{4-[5-carboxy-2-(4-chlorophenyl)benzyloxy]-2-fluorophenyl}-5-cyano-1-cyclohexylbenzimidazole(Example 437),

[1311]2-{4-[2-(4-chlorophenyl)-5-(dimethylcarbamoyl)benzyloxy]-2-fluorophenyl}-5-cyano-1-cyclohexylbenzimidazole(Example 438),

[1312]2-{4-[{N-(4-dimethylcarbamoyl)-N-(4-fluorophenyl)amino}-methyl]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 439),

[1313]2-{5-[bis(3-fluorophenyl)methyl]-2-fluoro-4-hydroxyphenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 440),

[1314]2-3-[bis(3-fluorophenyl)methyl]-2-fluoro-4-hydroxyphenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid (Example 441),

[1315]2-{4-[(3-dimethylcarbamoylphenyl)(4-fluorophenyl)methoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 442),

[1316]2-{4-[{3-(4-hydroxypiperidyl-1-ylcarbonyl)phenyl}(4-fluorophenyl)methoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 443),

[1317]1-{[2-{4-([4-(4-fluorophenyl)-2-methylthiazol-5-yl]methoxy)phenyl}-1-cyclohexylbenzimidazol-5-yl]carbonyl}-β-D-glucuronicacid (Example 444),

[1318]{[2-{4-[bis(3-fluorophenyl)methoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazol-5-yl]carbonyl}-β-D-glucuronicacid (Example 445),

[1319]2-{4-[2-(4-chlorophenyl)-5-(1,1-dioxoisothiazolidin-2-yl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride (Example 446),

[1320]2-{4-[2-(4-chlorophenyl)-5-(isopropylcarbamoyl)benzyloxy]phenyl}-3-cyclohexyl-3H-dimidazo[4,5-b]pyridine-6-carboxylicacid hydrochloride (Example 702), and

[1321]2-{4-[2-(4-chlorophenyl)-5-(pyrrolidin-1-ylcarbonyl)benzyloxy]-phenyl}-3-cyclohexyl-3H-imidazo[4,5-b]pyridine-6-carboxylicacid hydrochloride (Example 703).

[1322] (94) A pharmaceutical composition comprising a fused ringcompound of any of (42) to (93) above, or a pharmaceutically acceptablesalt thereof, and a pharmaceutically acceptable carrier.

[1323] (95) A hepatitis C virus polymerase inhibitor comprising a fusedring compound of any of (1) to (93) above, or a pharmaceuticallyacceptable salt thereof, and a pharmaceutically acceptable carrier.

[1324] (96) An anti-hepatitis C virus agent comprising a fused ringcompound of any of (1) to (93) above, or a pharmaceutically acceptablesalt thereof, and a pharmaceutically acceptable carrier.

[1325] (97) A therapeutic agent for hepatitis C comprising a fused ringcompound of any of (42) to (93) above, or a pharmaceutically acceptablesalt thereof, and a pharmaceutically acceptable carrier.

[1326] (98) An anti-hepatitis C virus agent comprising (a) theanti-hepatitis C virus agent of (96) above and (b) at least one agentselected from the group consisting of a different antiviral agent, anantiinflammatory agent and an immunostimulant.

[1327] (99) An anti-hepatitis C virus agent comprising (a) theanti-hepatitis C virus agent of (96) above and (b) interferon.

[1328] (100) A therapeutic agent for hepatitis C comprising (a) thehepatitis C virus polymerase inhibitor of (95) above and (b) at leastone agent selected from the group consisting of a different antiviralagent, an antiinflammatory agent and an immunostimulant.

[1329] (101) A therapeutic agent for hepatitis C comprising (a) thehepatitis C virus polymerase inhibitor of (95) above and (b) interferon.

[1330] (102) A benzimidazole compound of the following formula [III]

[1331] wherein R^(a36) is hydrogen atom or carboxyl-protecting group,R^(a37) is cyclopentyl or cyclohexyl, and R^(a38) is hydrogen atom orfluorine atom, or a salt thereof.

[1332] (103) A thiazole compound selected from the group consisting of4-(4-fluorophenyl)-5-hydroxymethyl-2-methylthiazole and4-(4-fluorophenyl)-5-chloromethyl-2-methylthiazole, or apharmaceutically acceptable salt thereof.

[1333] (104) A pharmaceutical composition comprising (a) the fusedcompound of the formula [I] of (1) above or a pharmaceuticallyacceptable salt thereof and (b) at least one agent selected from thegroup consisting of an antiviral agent other than the compound of (1)above, an antiinflammatory agent and an immunostimulant.

[1334] (105) A pharmaceutical composition comprising (a) the fusedcompound of the formula [I] of (1) above or a pharmaceuticallyacceptable salt thereof and (b) interferon.

[1335] (106) A method for treating hepatitis C, which comprisesadministering an effective amount of a fused ring compound of theformula [I] of (1) above, or a pharmaceutically acceptable salt thereof.

[1336] (107) The method of (106) above, further comprising administeringan effective amount of at least one agent selected from the groupconsisting of an antiviral agent other than the compound of (1) above,an antiinflammatory agent and an immunostimulant.

[1337] (108) The method of (106) above, further comprising administeringan effective amount of interferon.

[1338] (109) A method for inhibiting hepatitis C virus polymerase, whichcomprises administering an effective amount of a fused ring compound ofthe formula [I] of (1) above, or a pharmaceutically acceptable saltthereof.

[1339] (110) The method of (109) above, further comprising administeringan effective amount of at least one agent selected from the groupconsisting of an antiviral agent other than the compound of (1) above,an antiinflammatory agent and an immunostimulant.

[1340] (111) The method of (109) above, further comprising administeringan effective amount of interferon.

[1341] (112) Use of a fused ring compound of the above-mentioned formula[I] or a pharmaceutically acceptable salt thereof for the production ofa pharmaceutical agent for treating hepatitis C.

[1342] (113) Use of a fused ring compound of the above-mentioned formula[I] or a pharmaceutically acceptable salt thereof for the production ofa hepatitis C virus polymerase inhibitor.

[1343] (114) A pharmaceutical composition for the treatment of hepatitisC, which comprises a fused ring compound of the above-mentioned formula[I] or a pharmaceutically acceptable salt thereof, and apharmaceutically acceptable carrier.

[1344] (115) A pharmaceutical composition for inhibiting hepatitis Cvirus polymerase, which comprises a fused ring compound of theabove-mentioned formula [I] or a pharmaceutically acceptable saltthereof, and a pharmaceutically acceptable carrier.

[1345] (116) A commercial package comprising a pharmaceuticalcomposition of (114) above and a written matter associated therewith,the written matter stating that the pharmaceutical composition can orshould be used for treating hepatitis C.

[1346] (117) A commercial package comprising a pharmaceuticalcomposition of (115) above and a written matter associated therewith,the written matter stating that the pharmaceutical composition can orshould be used for inhibiting hepatitis C virus polymerase.

DETAILED DESCRIPTION OF THE INVENTION

[1347] The definitions of respective substituents and moieties used inthe present specification are as follows.

[1348] The halogen atom is a fluorine atom, chlorine atom, bromine atomor iodine atom, preferably fluorine atom, chlorine atom or bromine atom.

[1349] Particularly preferably, the halogen atom is fluorine atom at R⁵,R⁵′, R⁶, R⁶′, group A and group C, and fluorine atom or chlorine atom atX, Z, Z′, group B and group D.

[1350] The C₁₋₆ alkyl is straight chain or branched chain alkyl having 1to 6 carbon atoms, and is exemplified by methyl, ethyl, propyl,isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, pentyl, isopentyl,tert-pentyl, hexyl and the like.

[1351] Preferably, it is straight chain or branched chain alkyl having 1to 4 carbon atoms, and is particularly preferably methyl at R^(a7),R^(a8), R^(a9), R^(a15), R^(a16), R^(a17), R^(a29), R^(a33), R^(a35),R^(b6) and R^(b7) and methyl or tert-butyl at R^(b1), R^(b2), group Band group C.

[1352] The halogenated C₁₋₆ alkyl is the above-defined C₁₋₆ alkyl exceptthat it is substituted by the above-defined halogen atom. Preferably, itis halogenated alkyl wherein the alkyl moiety thereof is straight chainor branched chain alkyl having 1 to 4 carbon atoms. Examples thereofinclude fluoromethyl, difluoromethyl, trifluoromethyl, bromomethyl,chloromethyl, 1,2-dichloromethyl, 2,2-dichloromethyl,2,2,2-trifluoroethyl and the like.

[1353] The halogenated C₁₋₆ alkyl is particularly preferablytrifluoromethyl at group B.

[1354] The C₁₋₆ alkylene is straight chain alkylene having 1 to 6 carbonatoms, and is exemplified by methylene, ethylene, trimethylene,tetramethylene, pentamethylene or hexamethylene.

[1355] The C₁₋₆ alkylene is preferably methylene or ethylene at Y.

[1356] The C₂₋₆ alkenylene is straight chain alkenylene having 2 to 6carbon atoms, and is exemplified by vinylene, prooenylene, 1-butenylene,1,3-butadienylene and the like.

[1357] The C₂₋₆ alkenylene is preferably vinylene at Y.

[1358] The C₁₋₆ alkoxy is alkyloxy wherein the alkyl moiety thereof isthe above-defined C₁₋₆ alkyl. Preferably, it: is alkoxy wherein thealkyl moiety thereof is straight chain or branched chain alkyl having 1to 4 carbon atoms. Examples thereof include methoxy, ethoxy, propoxy,isopropyloxy, butoxy, isobutyloxy, tert-butyloxy, pentyloxy, hexyloxyand the like.

[1359] The C₁₋₆ alkoxy is particularly preferably methoxy at R^(a2)R^(a3), R^(a27), R^(a28), R^(a33), group A and group C.

[1360] The C₁₋₆ alkoxy C₁₋₆ alkoxy is that wherein C₁₋₆ alkoxy in theabove definition is substituted by C₁₋₆ alkoxy defined above and ispreferably that wherein the alkyl moiety thereof is straight chain orbranched chain alkyl having 1 to 4 carbon atoms. Specific examplesinclude methoxymethyl, ethoxymethyl, methoxyethoxy, methoxypropoxy,isopropyloxyethoxy and the like.

[1361] The group A is particularly preferably methoxyethoxy.

[1362] The C₁₋₆ alkanoyl is alkylcarbonyl wherein the alkyl moietythereof is the above-defined C₁₋₆ alkyl. Preferably, it is alkanoylwherein the alkyl moiety thereof is straight chain or branched chainalkyl having 1 to 4 carbon atoms. Examples thereof include acetyl,propionyl, butyryl, isobutyryl, pivaloyl and the like.

[1363] The C₁₋₆ alkanoyl is particularly preferably acetyl at R¹, R²,R³, R⁴, R^(a5), R^(a29), R^(b7) and group B.

[1364] The C₁₋₆ alkoxycarbonyl is alkyloxycarbonyl wherein the alkoxymoiety thereof is the above-defined C₁₋₆ alkoxy. Preferably, it isalkoxycarbonyl wherein the alkyl moiety thereof is straight chain orbranched chain alkyl having 1 to 4 carbon atoms. Examples thereofinclude methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl,isopropyloxycarbonyl, butoxycarbonyl, isobutyloxycarbonyl,tert-butyloxycarbonyl, pentyloxycarbonyl, hexyloxycarbonyl and the like.

[1365] The C₁₋₆ alkoxycarbonyl is particularly preferablymethoxycarbonyl or ethoxycarbonyl at R^(a10) and group A.

[1366] The C₁₋₆ alkylamino is alkylamino or dialkylamino wherein thealkyl moiety thereof is the above-defined C₁₋₆ alkyl. Preferably, it isalkylamino or dialkylamino wherein the alkyl moiety thereof is straightchain or branched chain alkyl having 1 to 4 carbon atoms. Examplesthereof include methylamino, ethylamino, propylamino, isopropylamino,butylamino, isobutylamino, tert-butylamino, pentylamino, hexylamino,dimethylamino, diethylamino, methylethylamino,N-isopropyl-N-isobutylamino and the like.

[1367] The C₁₋₆ alkylamino is particularly preferably methylamino atR^(a7), and particularly preferably dimethylamino at R^(a21) and groupA, and particularly preferably dimethylamino, ethylamino orisopropylamino at R^(a24).

[1368] The C₁₋₆ alkanoylamino is alkylcarbonylamino wherein the alkanoylmoiety thereof is the above-defined C₁₋₆ alkaroyl. Preferably, it isalkylcarbonylamino wherein the alkyl moiety thereof is straight chain orbranched chain alkyl having 1 to 4 carbon atoms. Examples thereofinclude acetylamino, propionylamino, butyrylamino, isobutyrylamino,pivaloylamino and the like.

[1369] The C₁₋₆ alkanoylamino is particularly preferably acetylamino atX and R^(a10).

[1370] The C₁₋₆ alkylsulfonyl is alkylsulfonyl wherein the alkyl moietythereof is the above-defined C₁₋₆ alkyl. Preferably, it is alkylsulfonylwherein the alkyl moiety thereof is straight chain or branched chainalkyl having 1 to 4 carbon atoms. Examples thereof includemethylsulfonyl, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl,butylsulfonyl, isobutylsulfonyl, tert-butylsulfonyl, pentylsulfonyl,hexylsulfonyl and the like.

[1371] The C₁₋₆ alkylsulfonyl is particularly preferably methylsulfonylat X and R^(a5).

[1372] The C₆₋₁₄ aryl is aromatic hydrocarbon having 6 to 14 carbonatoms. Examples thereof include phenyl, naphthyl, anthryl, indenyl,azulenyl, fluorenyl, phenanthryl and the like.

[1373] The C₆₋₁₄ aryl is preferably phenyl or naphthyl, particularlypreferably phenyl at the ring A, ring A′, ring B and ring B′.

[1374] The C₃₋₈ cycloalkyl is saturated cycloalkyl having 3 to 8,preferably 5 to 7, carbon atoms. Examples thereof include cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl.

[1375] The C₃₋₈ cycloalkyl is particularly preferably cyclohexyl at thering A, ring A′, ring B and ring B′.

[1376] The C₃₋₈ cycloalkenyl is cycloalkenyl having 3 to 8, preferably 5to 7, carbon atoms and has at least 1, preferably 1 or 2, doublebond(s). Examples thereof include cyclopropenyl, cyclobutenyl,cyclopentenyl, cyclopentadienyl, cyclohecenyl, 2,4-cyclohexadien-1-yl,2,5-cyclohexadien-1-yl, cycloheptenyl and cyclooctenyl and the like, butdo not include aryl (e.g., phenyl) or completely saturated cycloalkyl.

[1377] The C₃₋₈ cycloalkenyl is preferably cyclohexenyl at the ring Aand ring A′.

[1378] The heterocyclic group has, as an atom constituting the ring, 1to 4 heteroatom(s) selected from an oxygen atom, a nitrogen atom and asulfur atom, besides a carbon atom,, and includes saturated ring andunsaturated ring, monocyclic ring and fused ring having the number ofring atom constituting the ring of 3 to 14.

[1379] The heterocyclic group as a monocyclic ring includes, forexample, pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, 1,3,5-triazinyl,pyrrolyl, pyrazolyl, imidazolyl, 1,2,4-triazolyl, tetrazolyl, thienyl,furyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, thiadiazolyl,pyrrolinyl, pyrrolidinyl, imidazolidinyl, piperidyl, piperazinyl,morpholinyl, thiomorpholinyl, tetrahydropyranyl and the like.

[1380] The heterocyclic group includes the groups of the followingformulas.

[1381] wherein E¹ is an oxygen atom, a sulfur atom or N(—R^(a35)) E² isan oxygen atom, CH₂ or N(—R^(a35)), E³ is an oxygen atom or a sulfuratom, wherein R^(a35) is independently hydrogen atom or C₁₋₆ alkyl, f isan integer of 1 to 3, and h and h′ are the same or different and each isan integer of 1 to 3.

[1382] Specific examples of the heterocyclic group include

[1383] and the like.

[1384] Examples of the heterocyclic group as a fused ring includequinolyl, isoquinolyl, quinazolinyl, quinoxalyl, phthalazinyl,cinnolinyl, naphthyridinyl, 5,6,7,8-tetrahydroquinolyl, indolyl,benzimidazolyl, 2,3-dihydrobenzimidazolyl,2,3-dihydro-2-oxobenzimidazolyl, indolinyl, benzofuranyl, benzothienyl,benzoxazolyl, benzothiazolyl and the like.

[1385] Preferably, it is a heterocyclic group which is a 5-membered or a6-membered monocyclic group. Examples thereof include pyridyl,pyrazinyl, pyrimidinyl, pyridazinyl, 1,3,5-triazinyl, pyrrolyl,pyrazolyl, imidazolyl, 1,2,4-triazolyl, tetrazolyl, thienyl, furyl,oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, thiadiazolyl,pyrrolidinyl, piperidyl, piperazinyl

[1386] and the like.

[1387] At R¹, R², R³, R⁴, Z and group D, tetrazolyl and5-oxo-Δ²-1,2,4-oxadiazolin-3-yl are particularly preferable.

[1388] The heterocyclic group is preferably pyridyl, pyrazinyl,pyrimidinyl or pyridazinyl which is an aromatic group, and particularlypreferably pyridyl at the ring A and ring A′.

[1389] The heterocyclic group is particularly preferably pyridyl,pyrazinyl, pyrimidinyl, pyridazinyl, 1,3,5-triazinyl, pyrrolyl,pyrazolyl, imidazolyl, 1,2,4-triazolyl, tetrazolyl, thienyl, furyl,oxazolyl, isoxazolyl, thiazolyl, isothiazolyl or thiadiazolyl, which isan aromatic group, at the ring B and ring B′. More preferably it ispyridyl or thiazolyl, most preferably thiazolyl.

[1390] The C₆₋₁₄ aryl C₁₋₆ alkyl is arylalkyl wherein the alkyl moietythereof is the above-defined C₁₋₆ alkyl and the aryl moiety is theabove-defined C₆₋₁₄ aryl. Preferably, it is arylalkyl wherein the alkylmoiety thereof is straight chain alkyl having 1 to 4 carbon atoms andthe aryl moiety is phenyl. Examples thereof include benzyl, phenethyl,3-phenylpropyl, 2-phenylpropyl, 4-phenylbutyl and the like.

[1391] The C₆₋₁₄ aryl C₁₋₆ alkyl is particularly preferably benzyl atR^(a8) and R^(b6).

[1392] The glucuronic acid residue is glucuronic acid less any hydroxylgroup, preferably P-D-glucuronic acid substituted at 1-position.

[1393] The C₆₋₁₄ aryl C₁₋₆ alkyloxycarbonyl is arylalkyloxycarbonylwherein the C₆₋₁₄ aryl C₁₋₆ alkyl moiety thereof is the above-definedC₆₋₁₄ aryl C₁₋₆ alkyl. Preferably, it is arylalkyloxycarbonyl whereinthe alkyl moiety thereof is straight chain alkyl having 1 to 4 carbonatoms and the aryl moiety is phenyl. Examples thereof includebenzyloxycarbonyl, phenethyloxycarbonyl, 3-phenylpropyloxycarbonyl,2-phenylpropyloxycarbonyl, 4-phenylbutyloxycarbonyl and the like.

[1394] The C₆₋₁₄ aryl C₁₋₆ alkyloxycarbonyl is particularly preferablybenzyloxycarbonyl at R^(b7).

[1395] The optionally substituted C₁₋₆ alkyl is the above-defined C₁₋₆alkyl, preferably that wherein straight chain or branched chain alkylhaving 1 to 4 carbon atoms is optionally substituted with 1 to 3substituent(s), and includes unsubstituted alkyl. The substituent(s)is(are) selected from the above-defined halogen atom, hydroxyl group,carboxyl, amino, the above-defined C₁₋₆ alkoxy, the above-defined C₁₋₆alkoxy C₁₋₆ alkoxy, the above-defined C₁₋₆ alkoxycarbonyl and theabove-defined C₁₋₆ alkylamino. Examples of optionally substituted C₁₋₆alkyl include methyl, ethyl, propyl, isopropyl, butyl, isobutyl,sec-butyl, tert-butyl, pentyl, isopentyl, tert-pentyl, neopentyl,1-ethylpropyl, hexyl, trifluoromethyl, hydroxymethyl, 2-hydroxyethyl,3-hydroxypropyl, 4-hydroxybutyl, 1-hydroxy-1-methylethyl,1-hydroxypropan-2-yl, 1,3-dihydroxypropan-2-yl,1-hydroxy-2-methylpropan-2-yl, carboxylmethyl, 2-carboxylethyl,methoxymethyl, methoxyethyl, methoxyethoxyethyl, ethoxycarbonylmethyl,2-ethoxycarbonylethyl, 2-dimethylaminoethyl and the like.

[1396] Preferably, the optionally substituted C₁₋₆ alkyl is methyl,1-hydroxy-1-methylethyl, carboxylmethyl or 2-dimethylaminoethyl at R¹,R², R³ and R⁴, methyl or trifluoromethyl at R⁵, R⁵′, R⁶ and R⁶′, methylat R⁷, R⁸, R^(a25), R^(a31) and R⁵, methyl, ethyl or isopropyl atR^(a24), methyl or isopropyl at R^(a18), methyl or ethyl at R^(a1) andR^(a19), methyl, carboxylmethyl or 2-dimethylaminoethyl at R^(a2) andR^(a3), methyl or carboxylmethyl at R^(a6), methyl, ethyl, isopropyl,butyl or trifluoromethyl at X, methyl, ethyl, isopropyl, butyl,isobutyl, tert-butyl, isopentyl, neopentyl, 1-ethylpropyl orcarboxylmethyl at R^(a10), methyl, ethyl, propyl, isopropyl, butyl,isobutyl, trifluoromethyl, 2-hydroxyethyl or carboxylmethyl at R^(a11),methyl or 4-hydroxybutyl at R^(a12), methyl, ethyl, isopropyl, butyl,2-hydroxyethyl, 4-hydroxybutyl, ethoxycarbonylmethyl,2-(ethoxycarbonyl)ethyl or 2-dimethylaminoethyl at R^(a13), methyl,propyl, butyl, isopentyl, trifluoromethyl, hydroxymethyl,2-hydroxyethyl, 3-hydroxypropyl, methoxyethyl, methoxyethoxyethyl orcarboxymethyl at R^(a20), methyl or ethyl at R^(a22) and R^(a23), methylisopropyl or tert-butyl at R^(a26), methyl, ethyl, propyl, isopropyl,butyl, tert-butyl, isobutyl, 2-hydroxyethyl 1-hydroxypropan-2-yl,1-hydroxy-2-methylpropan-2-yl or carboxylmethyl at R^(a27) and R^(a28),and methyl, ethyl, propyl, isopropyl, tert-butyl, trifluoromethyl,hydroxymethyl, 2-hydroxyethyl, 2-carboxylethyl, methoxymethyl orethoxycarbonylmethyl at Z, Z′ and group D.

[1397] It is particularly preferably, trifluoromethyl at R⁵, R⁵′, R⁶ andR⁶, methyl or tert-butyl at R^(a26), methyl, tert-butyl, trifluoromethylor hydroxymethyl at Z, Z′ and group D, and methyl at other substituents.

[1398] The optionally substituted C₂₋₆ alkenyl is that wherein straightchain or branched chain alkenyl having 2 to 6 carbon atoms is optionallysubstituted by 1 to 3 substituent(s), and includes unsubstitutedalkenyl. The substituent(s) is (are) selected from the above-definedhalogen atom, hydroxyl group, carboxyl, amino, the above-defined C₁₋₆alkoxy, the above-defined C₁₋₆ alkoxy C₁₋₆ alkoxy, the above-definedC₁₋₆ alkoxycarbonyl and the above-defined C₁₋₆ alkylamino. Examples ofoptionally substituted C₂₋₆ alkenyl include vinyl, allyl, 1-propenyl,isopropenyl, 1-butenyl, 2-butenyl, 1,3-butadienyl, 2-isopentenyl,3-isohexenyl, 4-methyl-3-pentenyl, 2-carboxylethenyl and the like.

[1399] The optionally substituted C₂₋₆ alkenyl is preferably2-carboxylethenyl at X, and preferably 2-isopentenyl, 3-isohexenyl or4-methyl-3-pentenyl at R^(a20).

[1400] The optionally substituted C₂₋₆ alkynyl is that wherein straightchain or branched chain alkynyl having 2 to 6 carbon atoms is optionallysubstituted by 1 to 3 substituent(s), and includes unsubstitutedalkynyl. The substituent(s) is(are) selected from the above-definedhalogen atom, hydroxyl group, carboxyl, amino, the above-defined C₁₋₆alkoxy, the above-defined C₁₋₆ alkoxycarbonyl and the above-defined C₁₋₆alkylamino. Examples thereof include ethynyl, 1-propynyl, 2-propynyl,3-butynyl and the like.

[1401] The optionally substituted C₂₋₆ alkynyl is preferably 2-propynylat R^(a20).

[1402] The C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from group B is that wherein the above-defined C₆₋₁₄ aryl isoptionally substituted by 1 to 5 substituent(s), and includesunsubstituted aryl. The substituent(s) is(are) selected from theabove-defined halogen atom, cyano, nitro, the above-defined C₁₋₆ alkyl,the above-defined halogenated C₁₋₆ alkyl, the above-defined C₁₋₆alkanoyl, —(CH₂)_(r)—COOR^(b1), —(CH₂)_(r)—CONR^(b1)R^(b2),—(CH₂)_(r)—NR^(b1)R^(b2), —(CH₂)_(r)—NR^(b1)—COR^(b2),—(CH₂)_(r)—NHSO₂R^(b1), —(CH₂)_(r)—OR^(b1), —(CH₂)_(r)—SR^(b1),—(CH₂)_(r)—SO₂R^(b1) and —(CH₂)_(r)—SO₂NR^(b1)R^(b2) (wherein R^(b1) andR^(b2) are each independently hydrogen atom or the above-defined C₁₋₆alkyl and r is 0 or an integer of 1 to 6).

[1403] Examples thereof include phenyl, naphthyl, anthryl, indenyl,azulenyl, fluorenyl, phenanthryl, 3-fluorophenyl, 4-fluorophenyl,3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl, 3,5-dichlorophenyl,pentafluorophenyl, 4-methylphenyl, 4-tert-butylphenyl,2-trifluoromethylphenyl, 4-trifluoromethylphenyl, 4-nitrophenyl,4-cyanophenyl, 4-acetylphenyl, 4-carboxylphenyl, 4-carbamoylphenyl,4-aminophenyl, 4-dimethylaminophenyl, 4-acetylaminophenyl,4-(methylsulfonylamino)phenyl, 4-methoxyphenyl, 3,4,5-trimethoxyphenyl,4-methylthiophenyl, 4-methylsulfonylphenyl, 4-aminosulfonylphenyl,3-nitro-4-methoxyphenyl and 4-nitro-3-methoxyphenyl.

[1404] The aryl moiety is preferably phenyl, the group B here ispreferably the above-defined halogen atom, nitro, the above-defined C₁₋₆alkyl, the above-defined halogenated C₁₋₆ alkyl or —(CH₂)_(r)—OR^(b1).Examples of group B include fluorine atom, chlorine atom, nitro, methyl,tert-butyl, trifluoromethyl and methoxy. Particularly preferably, it isfluorine atom or chlorine atom.

[1405] With regard to “C₆₋₁₄ aryl optionally substituted by 1 to 5substituent(s) selected from group B”, it is preferably phenyl,4-tert-butylphenyl, 4-fluorophenyl, 3-chlorophenyl, 4-chlorophenyl,4-methoxyphenyl or 4-trifluoromethylphenyl at R^(a12), R^(a27) andR^(a28), phenyl at R^(a14), R^(a22), R^(a23), R^(a26) and R^(b5), phenylor 3-fluorophenyl at R^(a18), phenyl or 2,4-dichlorophenyl at R^(a20),phenyl, 4-chlorophenyl, 4-trifluoromethylphenyl, 3,5-dichlorophenyl,3-nitro-4-methoxyphenyl or 4-nitro-3-methoxyphenyl at R^(a24), andphenyl or 4-methylphenyl at R^(a25).

[1406] It is particularly preferably phenyl at other substituents.

[1407] The C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from group D is that wherein the above-defined C₆₋₁₄ aryl isoptionally substituted by 1 to 5 substituent(s), and includesunsubstituted aryl. The substituent(s) is(are) selected from theabove-mentioned group D (substituents shown under (a) to (q)).

[1408] Examples of group D here include fluorine atom, chlorine atom,bromine atom, nitro, cyano, methyl, ethyl, propyl, isopropyl,tert-butyl, trifluoromethyl, hydroxymethyl, 2-hydroxyethyl,methoxymethyl, 2-carboxylethyl, methoxycarbonylmethyl,ethoxycarbonylmethyl, acetyl, carboxyl, methoxycarbonyl, ethoxycarbonyl,carbamoyl, methylaminocarbonyl, isopropylaminocarbonyl,dimethylaminocarbonyl, diethylaminocarbonyl,(2-hydroxyethyl)aminocarbonyl, (carboxylmethyl)aminocarbonyl, hydroxylgroup, methoxy, ethoxy, propyloxy, isopropyloxy, isopentyloxy,2-isopentenyloxy, 3-isohexenyloxy, 4-methyl-3-pentenyloxy,2-propynyloxy, hydroxymethyloxy, carboxylmethyloxy,(dimethylaminocarbonyl)methyloxy, amino, methylamino, dimethylamino,diethylamino, acetylamino, methylsulfonylamino, methylthio,methylsulfonyl, methylsulfinyl, aminosulfonyl, methylaminosulfonyl,dimethylaminosulfonyl and tetrazolyl.

[1409] Examples of C₆₋₁₄ aryl optionally substituted by 1 to 5substituent(s) selected from group D include phenyl, naphthyl, anthryl,indenyl, azulenyl, fluorenyl, phenanthryl, 3-fluorophenyl,4-fluorophenyl, 3-chlorophenyl, 4-chlorophenyl, 2,4-dichlorophenyl,3,5-dichlorophenyl, 4-bromophenyl, 4-nitrophenyl, pentafluorophenyl,4-methylphenyl, 4-tert-butylphenyl, 2-trifluoromethylphenyl,4-trifluoromethylphenyl, 4-(hydroxymethyl)phenyl,4-(methoxymethyl)phenyl, 4-(2-carboxylethyl)phenyl, 3-carboxylphenyl,4-carboxylphenyl, 4-methoxyphenyl, 3,4,5-trimethoxyphenyl,4-carbamoylphenyl, 4-methylthiophenyl, 4-(dimethylaminocarbonyl)phenyl,4-methylsulfonylphenyl, 4-acetylaminophenyl, 4-cyanophenyl,4-acetylphenyl, 4-aminophenyl, 4-dimethylaminophenyl,4-(methylsulfonylamino)phenyl, 4-methylsulfinylphenyl,4-aminosulfonylphenyl and 3-nitro-4-methoxyphenyl,4-nitro-3-methoxyphenyl and 4-tetrazol-5-ylphenyl.

[1410] At Z and Z′, the aryl moiety is preferably phenyl, and group Dhere is preferably the above-defined halogen atom, nitro, theabove-defined optionally substituted C₁₋₆ alkyl, —(CH₂)_(t)—COOR^(a19),—(CH₂)_(t)CONR^(a27)R^(a28), —(CH₂)_(t)—OR^(a20),—(CH₂)_(t)—NR^(a29)CO—R^(a24), —(CH₂)_(t)—S(O)_(q)—R^(a25) or—(CH₂)_(t)—SO₂—NHR^(a26).

[1411] Examples of C₆₋₁₄ aryl optionally substituted by 1 to 5substituent(s) selected from group D preferably include phenyl,3-fluorophenyl, 4-fluorophenyl, 3-chlorophenyl, 4-chlorophenyl,3,5-dichlorophenyl, 4-bromophenyl, 4-nitrophenyl, 4-methylphenyl,4-tert-butylphenyl, 2-trifluoromethylphenyl, 4-trifluoromethylphenyl,4-(hydroxymethyl)phenyl, 4-(methoxymethyl)phenyl,4-(2-carboxylethyl)phenyl, 3-carboxylphenyl, 4-carboxylphenyl,4-methoxyphenyl, 3,4,5-trimethoxyphenyl, 4-carbamoylphenyl,4-methylthiophenyl, 4-(dimethylaminocarbonyl)phenyl,4-methylsulfonylphenyl, 4-acetylaminophenyl, 4-methylsulfinylphenyl,4-aminosulfonylphenyl, 4-cyanophenyl and 4-tetrazolylphenyl.

[1412] Particularly preferably, it is the above-defined halogen atom,the above-defined optionally substituted C₁₋₆ alkyl,—(CH₂)_(t)—COOR^(a19), —(CH₂)_(t)—CONR^(a27)R^(a28), —(CH₂)_(t)—OR^(a20)or —(CH₂)_(t)—S(O)_(q)—R^(a25), which is specifically fluorine atom,chlorine atom, bromine atom, nitro, methyl, tert-butyl, carboxyl,trifluoromethyl, hydroxymethyl, methoxymethyl, 2-carboxylethyl, methoxy,carbamoyl, methylthio, dimethylaminocarbonyl, methylsulfonyl oracetylamino. More preferably, it is fluorine atom, chlorine atom,m(ethyl, tert-butyl, carboxyl, methoxy, carbamoyl, methylthio,dimethylaminocarbonyl, methylsulfonyl or acetylamino, most preferablyfluorine atom or chlorine atom.

[1413] The heterocyclic group optionally substituted by 1 to 5substituent(s) selected from group B is that wherein the above-definedheterocyclic group is optionally substituted by 1 to 5 substituent(s),and includes unsubstituted heterocyclic group. The substituent(s)is(are) selected from the above-defined halogen atom, cyano, nitro, theabove-defined C₁₋₆ alkyl, the above-defined halogenated C₁₋₆ alkyl, theabove-defined C₁₋₆ alkanoyl, —(CH₂)_(r)COOR^(b1),—(CH₂)_(r)—CONR^(b1)R^(b2), —(CH₂)_(r)—NR^(b1)R^(b2), —(CH₂)_(r)—NR^(b1)—COR^(b2), —(CH₂)_(r)—NHSO₂R^(b1), —(CH₂)_(r)—OR^(b1),—(CH₂)_(r)—SR^(b1), —(CH₂)_(r)—SO₂R^(b1) and —(CH₂)_(r)—SO₂NR^(b1)R^(b2)wherein R^(b1) and R^(b2) are each independently hydrogen atom or theabove-defined C₁₋₆ alkyl and r is 0 or an integer of 1 to 6.

[1414] Examples thereof include 2-pyridyl, 3-pyridyl, 4-pyridyl,3-fluoropyridin-4-yl, 3-chloropyridin-4-yl, 4-chloropyridin-3-yl,pyrazinyl, pyrimidinyl, pyridazinyl, 1,3,5-triazinyl, pyrrolyl,pyrazolyl, imidazolyl, 1,2,4-triazolyl, tetrazolyl, 2-thienyl,3-thienyl, furyl, oxazolyl, 2-methyloxazol-4-yl, isoxazolyl, thiazolyl,2-methylthiazol-4-yl, 2,5-dimethylthiazol-4-yl,2,4-dimethylthiazol-5-yl, isothiazolyl, thiadiazolyl, pyrrolinyl,pyrrolidinyl, 3-hydroxypyrrolidinyl, imidazolidinyl, azetidinyl,piperidyl, 3-hydroxypiperidino, 4-hydroxypiperidino,3,4-dihydroxypiperidino, 4-methoxypiperidino, 4-carboxypiperidino,4-(hydroxymethyl)piperidino, 2-oxopiperidino, 4-oxopiperidino,2,2,6,6-tetramethylpiperidino, 2,2,6,6-tetramethyl-4-hydroxypiperidino,N-methylpiperidin-4-yl, N-(tert-butoxycarbonyl)piperidin-4-yl,N-acetylpiperidin-4-yl, N-methylsulfonylpiperidin-4-yl, piperazinyl,4-methylpiparazinyl, 4-methylsulfonylpiperazinyl, morpholinyl,thiomorpholinyl, 1-oxothiomorpholin-4-yl, 1,1-dioxothiomorpholin-4-yl,tetrahydropyranyl, quinolyl, isoquinolyl, quinazolinyl, quinoxalyl,phthalazinyl, cinnolinyl, naphthyridinyl, 5,6,7,8-tetrahydroquinolyl,indolyl, benzimidazolyl, indolinyl, benzofuranyl, benzothienyl,benzoxazolyl, benzothiazolyl,

[1415] and the like.

[1416] The heterocyclic moiety is preferably a heterocyclic group whichis a 5-membered or a 6-membered monocyclic group. Examples thereofinclude pyridyl, pyrazinyl, pyrimidinyl, pyridiazinyl, 1,3,5-triazinyl,pyrrolyl, pyrazolyl, imidazolyl, 1,2,4-triazolyl, tetrazolyl, thienyl,furyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, thiadiazolyl,pyrrolidinyl, piperidyl, piperazinyl, morpholinyl, thiomorpholinyl andtetrahydropyranyl, and the group B here is preferably the above-definedhalogen atom, the above-defined C₁₋₆ alkyl, the above-definedhalogenated C₁₋₆ alkyl, the above-defined C₁₋₆ alkanoyl,—(CH₂)_(r)—COOR^(b1), —(CH₂)_(r)—CONR^(b1)R^(b2) or —(CH₂)_(r)—OR^(b1).

[1417] Examples of heterocyclic group optionally substituted by 1 to 5substituent(s) selected from group B preferably include piperidino,4-methylpiperidino, 2,6-dimethylpiperidino, 4-hydroxypiperidino,1-piperazinyl, 1-(methylsulfonyl)piperidin-4-yl, 1-pyrrolidinyl,morpholino, 4-thiomorpholinyl, tetrahydropyranyl, pyridyl, thiazolyl,

[1418] Particularly preferably, it is piperidino, 4-methylpiperidino,2,6-dimethylpiperidino, 4-hydroxypiperidino, 1-piperazinyl,1-pyrrolidinyl, morpholino or 4-thiomorpholinyl at R^(a18),tetrahydropyranyl or 4-hydroxypiperidino at R^(a20), piperidino,4-hydroxypiperidino or 3,4-dihydroxypiperidino at R^(a21), pyridyl ormorpholino at R^(a24), pyridyl or 4-hydroxypiperidino at R^(a25),pyridyl or thiazolyl at R^(a26) and at R^(a27) and R^(a28), it is1-(methylsulfonyl)piperidin-4-yl, 3-hydroxypyrrolidinyl,3-hydroxypiperidino, 4-hydroxypiperidino, 3,4-dihydroxypiperidino,4-methoxypiperidino, 4-carboxypiperidino, 4-(hydroxymethyl)piperidino,2-oxopiperidino, 4-oxopiperidino, 2,2,6,6-tetramethylpiperidino,2,2,6,6-tetramethyl-4-hydroxypiperidino, 4-methylsulfonylpiperazinyl,1-oxothiomorpholin-4-yl or 1,1-dioxothiomorpholin-4-yl, and2-oxazolin-2-yl at R^(a22) and R^(a23).

[1419] The heterocyclic group optionally substituted by(1 to 5substituent(s) selected from group D is that wherein the above-definedheterocyclic group is optionally substituted by 1 to 5 substituent(s),and includes unsubstituted heterocyclic group. The substituent(s)is(are) selected from the substituent(s) of the above-mentioned group D(substituents shown under (a) to (q)).

[1420] Examples of the group D here include the substituent(s)exemplified for C₆₋₁₄ aryl optionally substituted by 1 to 5substituent(s) selected from group D.

[1421] Examples of heterocyclic group optionally substituted by 1 to 5substituent(s) selected from group D include 2-pyridyl, 3-pyridyl,4-pyridyl, 3-fluoropyridin-4-yl, 3-chloropyridin-4-yl,4-chloropyridin-3-yl, pyrazinyl, pyrimidinyl, pyridazinyl,1,3,5-triazinyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,4-triazolyl,tetrazolyl, 2-thienyl, 3-thienyl, furyl, oxazolyl, 2-methyloxazol-4-yl,isoxazolyl, thiazolyl, 2-methylthiazol-4-yl, 2,5-dimethylthiazol-4-yl,2,4-dimethylthiazol-5-yl, isothiazolyl, thiadiazolyl, pyrrolinyl,pyrrolidinyl, imidazolidinyl, piperidyl, N-methylpiperidin-4-yl,N-(tert-butoxycarbonyl)piperidin-4-yl, N-acetylpiperidin-4-yl,N-methylsulfonylpiperidin-4-yl, piperazinyl, morpholinyl,thiomorpholinyl, tetrahydropyranyl, quinolyl, isoquinolyl, quinazolinyl,quinoxalyl, phthalazinyl, cinnolinyl, naphthyridinyl,5,6,7,8-tetrahydroquinolyl, indolinyl, benzimidazolyl, indolinyl,benzofuranyl, benzothienyl, benzoxazolyl, benzothiazolyl

[1422] and the like.

[1423] In addition, the heterocyclic group may be substituted at the 3-,4-, 5- or 6-position of 2-pyridyl, at the 2-, 4-, 5- or 6-position of3-pyridyl, at the 2-, 3-, 5- or 6-position of 4-pyridinyl, at the 3-, 4-or 5-position of 2-thienyl, or at the 2-, 4- or 5-position of 3-thienyl,by fluorine atom, chlorine atom, bromine atom, nitro, methyl,tert-butyl, carboxyl, trifluoromethyl, hydroxymethyl, methoxymethyl,2-carboxylethyl, methoxy, carbamoyl, methylthio, dimethylaminocarbonyl,methylsulfonyl, amino or acetylamino.

[1424] At Z and Z′, the heterocyclic moiety is preferably a heterocyclicgroup which is a 5-membered or 6-membered monocyclic group. Examplesthereof include pyridyl, pyrazinyl, pyrimidinyl, pyridazinyl,1,3,5-triazinyl, pyrrolyl, 2-oxopyrrolidinyl, 2-oxopiperidyl, pyrazolyl,imidazolyl, 2-imidazolinyl, 2-oxoimidazolidinyl, 1,2,4-triazolyl,tetrazolyl, thienyl, furyl, oxazolyl, isoxazolyl, 2-oxazolinyl,thiazolyl, isothiazolyl, 1,1-dioxoisothiazolidinyl, thiadiazolyl,pyrrolidinyl, piperidyl, piperazinyl, morpholinyl, thiomorpholinyl,tetrahydropyranyl, Δ²-1,2,4-oxadiazolyl, 5-oxo-Δ²-1,2,4-oxadiazolyl,5-oxo-Δ²-1,2,4-thiadiazolinyl and 2-oxo-3H-1,2,3,5-oxathiadiazolinyl.The group D here is preferably the above-defined halogen atom, nitro,the above-defined optionally substituted C₁₋₆ alkyl,—(CH₂)_(t)—COOR^(a19), —(CH₂)_(t)—CONR^(a27)R^(a28),—(CH₂)_(t)—OR^(a20), —(CH₂)_(t)—NR^(a29)CO—R^(a24),—(CH₂)_(t)—S(O)_(q)—R^(a25) or —(CH₂)_(t)—SO₂—NHR^(a26).

[1425] Examples of heterocyclic group optionally substituted by 1 to 5substituent(s) selected from group D preferably include piperidino,4-hydroxypiperidino, 2-oxopiperidin-1-yl, 1-piperazinyl, 1-pyrrolidinyl,2-oxopyrrolidin-1-yl, morpholino, 4-thiomorpholinyl,4-tetrahydropyranyl, 3-pyridyl, 2-pyrimidinyl, 2-imidazolin-2-yl,2-oxoimidazolidin-1-yl, 2-oxooxazolidin-1-yl, 5-tetrazolyl, 2-thiazolyl,4-thiazolyl, 5-thiazolyl, 2-methylthiazol-4-yl, 5-methylthiazol-2-yl,2-aminothiazol-4-yl, 3-methyl-1,2,4-oxadiazol-5-yl,1,1-dioxoisothiazolidin-2-yl, 4,4-dimethyl-Δ²-oxazolin-2-yl, 2-thienyl,5-chlorothiophen-2-yl, 5-methyloxazol-2-yl,5-oxo-Δ²-1,2,4-oxadiazolin-3-yl, 5-oxo-Δ²-1,2,4-thiadiazolin-3-yl and2-oxo-3H-1,2,3,5-oxathiazolin-4-yl.

[1426] Particularly preferably, it is pyridyl, pyrimidinyl, tetrazolyl,thienyl, piperidyl, 2-oxopiperidin-1-yl, 2-oxopyrrolidin-1-yl,2-imidazolin-2-yl, 2-oxoimidazolidin-1-yl, 2-oxooxazolidin-1-yl,2-methylthiazol-4-yl, 5-methylthiazol-2-yl, 2-aminothiazol-4-yl,3-methyl-1,2,4-oxadiazol-5-yl, 1,1-dioxoisothiazolidin-2-yl,4,4-dimethyl-Δ²-oxazolin-2-yl, 5-chlorothiophen-2-yl,5-methyloxazol-2-yl, 5-oxo-Δ²-1,2,4-oxadiazolin-3-yl,5-oxo-Δ²-1,2,4-thiadiazolin-3-yl or2-oxo-3H-1,2,3,5-oxathiadiazolin-4-yl, more preferably2-oxopyrrolidin-1-yl.

[1427] The C₃₋₈ cycloalkyl optionally substituted by 1 to 5substituent(s) selected from group C is that wherein the above-definedC₃₋₈ cycloalkyl is optionally substituted by the 1 to 5 substituent(s)selected from hydroxyl group, the above-defined halogen atom, theabove-defined C₁₋₆ alkyl and the above-defined C₁₋₆ alkoxy, which may beunsubstituted. Examples thereof include cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, cycloheptyl, 4-fluorocyclohexyl,2-methylcyclopentyl, 3-methylcyclohexyl, 4-methylcyclohexyl,4,4-dimethylcyclohexyl, 3,5-dimethylcyclohexyl, 4-tert-butylcyclohexyl,4-hydroxycyclohexyl, 4-methoxyayclohexyl and2,3,4,5,6-pentafluorocyclohexyl.

[1428] The cycloalkyl moiety is preferably cyclopentyl or cyclohexyl,particularly preferably cyclohexyl.

[1429] At the ring Cy and ring Cy′, the C₃₋₈ cycloalkyl optionallysubstituted by 1 to 5 substituent(s) selected from group C is preferablycyclopentyl, cyclohexyl, 4-fluorocyclohexyl, 4-methylcyclohexyl,4,4-dimethylcyclohexyl, 4-tert-butylcyclohexyl, 4-hydroxycyclohexyl or4-methoxycyclohexyl, more preferably cyclopentyl or cyclohexyl,particularly preferably cyclohexyl.

[1430] The C₃₋₈ cycloalkyl optionally substituted by 1 to 5substituent(s) selected from the above group B is that wherein theabove-defined C₃₋₈ cycloalkyl is optionally substituted by 1 to 5substituent(s), and includes unsubstituted cycloalkyl. The substituentsare selected from the above group B.

[1431] Specific examples thereof include cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, cycloheptyl, 4-fluorocyclohexyl,2-methylcyclopentyl, 3-methylcyclohexyl, 4-methylcyclohexyl,4,4-dimethylcyclohexyl, 3,5-dimethylcyclohexyl, 4-tert-butylcyclohexyl,4-hydroxycyclohexyl, 4-methoxycyclohexyl and2,3,4,5,6-pentafluorocyclohexyl.

[1432] Also exemplified are those wherein cyclopentyl or cyclohexyl issubstituted by fluorine atom, chlorine atom, bromine atom, nitro,methyl, tert-butyl, carboxyl, trifluoromethyl, hydroxymethyl,methoxymethyl, 2-carboxylethyl, methoxy, carbamoyl, methylthio,dimethylaminocarbonyl, methylsulfonyl or acetylamino.

[1433] At cycloalkyl moiety, it is preferably cyclopropyl, cyclobutyl,cyclopentyl or cyclohexyl. As the C₃₋₈ cycloalkyl optionally substitutedby 1 to 5 substituent(s) selected from the above group B, it isparticularly preferably cyclopropyl, cyclobutyl, cyclohexyl or4-hydroxycyclohexyl at R^(a27) and R^(a28).

[1434] The C₃₋₈ cycloalkyl optionally substituted by 1 to 5substituent(s) selected from group D is that wherein the above-definedC₃₋₈ cycloalkyl is optionally substituted by 1 to 5 substituent(s), andincludes unsubstituted cycloalkyl. The substituent(s) is(are) selectedfrom the substituent(s) of the above-mentioned group D (substituentsshown under (a) to (q)).

[1435] The group D here includes the substituents recited with regard toC₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s) selected fromgroup D.

[1436] Examples thereof include cyclopropyl, cyclobutyl, cyclopentyl,cyclohexyl, cycloheptyl, 4-fluorocyclohexyl, 2-methylcyclopentyl,3-methylcyclohexyl, 4-methylcyclohexyl, 4,4-dimethylcyclohexyl,3,5-dimethylcyclohexyl, 4-tert-butylcyclohexyl, 4-hydroxycyclohexyl,4-methoxycyclohexyl and 2,3,4,5,6-pentafluorocyclohexyl.

[1437] The group D may be, for example, cyclopentyl or cyclohexylsubstituted by fluorine atom, chlorine atom, bromine atom, nitro,methyl, tert-butyl, carboxyl, trifluoromethyl, hydroxymethyl,methoxymethyl, 2-carboxylethyl, methoxy, carbamoyl, methylthio,dimethylaminocarbonyl, methylsulfonyl or acetylamino.

[1438] The cycloalkyl moiety is preferably cyclopentyl or cyclohexyl,and at Z and Z′, it is particularly preferably cyclohexyl.

[1439] The optionally substituted C₃₋₈ cycloalkenyl is that wherein theabove-defined C₃₋₈ cycloalkenyl is optionally substituted bysubstituent(s) selected from hydroxyl group, the above-defined halogenatom, the above-defined C₁₋₆ alkyl and the above-defined C₁₋₆ alkoxy,which may be unsubstituted. Examples thereof include cyclopropenyl,cyclobutenyl, cyclopentenyl, cyclopentadienyl, cyclohexenyl,4-fluoro-2-cyclohexenyl, 4-methyl-2-cyclohexenyl,4-methyl-3-cyclohexenyl, 2,4-cyclohexadien-1-yl, 2,5-cyclohexadien-1-yl,cycloheptenyl and cyclooctenyl and the like, but do not include aryl(e.g., phenyl) or completely saturated cycloalkyl.

[1440] The optionally substituted C₃₋₈ cycloalkenyl is particularlypreferably cyclohexenyl at the ring Cy.

[1441] The C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from group B is that wherein the above-definedC₆₋₁₄ aryl C₁₋₆ alkyl is optionally substituted by 1 to 5substituent(s), and includes unsubstituted arylalkyl. The substituent(s)is(are) selected from the above-mentioned group B.

[1442] Examples thereof include benzyl, 1-naphthylmethyl,2-naphthylmethyl, phenethyl, 3-phenylpropyl, 2-phenylpropyl,3-fluorobenzyl, 4-fluorobenzyl, 3-chlorobenzyl, 4-chlorobenzyl,2,4-dichlorobenzyl, 3,5-dichlorobenzyl, pentafluorobenzyl,4-methylbenzyl, 4-tert-butylbenzyl, 2-trifluoromethylbenzyl,4-trifluoromethylbenzyl, 4-nitrobenzyl, 4-cyanobenzyl, 4-acetylbenzyl,4-carboxylbenzyl, 4-carbamoylbenzyl, 4-aminobenzyl,4-dimethylaminobenzyl, 4-acetylaminobenzyl,4-(methylsulfonylamino)benzyl, 4-methoxybenzyl, 3,4,5-trimethoxybenzyl,4-methylthiobenzyl, 4-methylsulfonylbenzyl, 4-aminosulfonylbenzyl,3-nitro-4-methoxybenzyl and 4-nitro-3-methoxybenzyl.

[1443] The C₆₋₁₄ aryl C₁₋₆ alkyl moiety is preferably benzyl orphenethyl, particularly preferably benzyl. The group B is preferably theabove-defined halogen atom, nitro, the above-defined C₁₋₆ alkyl, theabove-defined halogenated C₁₋₆ alkyl or —(CH₂)_(r)—OR^(b1). Examplesthereof include fluorine atom, chlorine atom, nitro, methyl, tert-butyl,trifluoromethyl, methoxy or trifluoromethyloxy, particularly preferablyfluorine atom or chlorine atom.

[1444] The specific C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to5 substituent(s) selected from group B at R and R is preferably benzyl,phenethyl, 3-chlorobenzyl, 4-chloro-3benzyl, 4-tert-butylbenzyl or3-trifluoromethylbenzyl, it is preferably benzyl at R^(a1), R^(a19),R^(a27), R^(a28), R^(a31) and R^(b5), it is preferably benzyl,phenethyl, 4-fluorobenzyl, 2-chlorobenzyl, 3-chlorobenzyl,4-chlorobenzyl, 4-tert-butylbenzyl or 4-trifluoromethylbenzyl atR^(a20), and 4-chlorobenzyl, 3,5-dichlorobenzyl or4-trifluoromethylbenzyl at R^(a22) and R^(a23).

[1445] It is particularly preferably benzyl at other substituents.

[1446] The C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from group D is that wherein the above-definedC₆₋₁₄ aryl C₁₋₆ alkyl is optionally substituted by 1 to 5substituent(s), and includes unsubstituted aryl. The substituent(s)is(are) selected from the substituent(s) of the above-mentioned group D(substituents shown under (a) to (q)).

[1447] Examples of group D include fluorine atom, chlorine atom, bromineatom, nitro, cyano, methyl, ethyl, propyl, isolpropyl, tert-butyl,trifluoromethyl, hydroxymethyl, 2-hydroxyethyl, methoxymethyl,2-carboxylethyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, acetyl,carboxyl, methoxycarbonyl, ethoxycarbonyl, carbamoyl,methylaminocarbonyl, isopropylaminocarbonyl, dimethylaminocarbonyl,diethylaminocarbonyl, (2-hydroxyethyl)aminocarbonyl,(carboxylmethyl)aminocarbonyl, hydroxyl group, methoxy, ethoxy,isopropyloxy, hydroxymethyloxy, carboxylmethyloxy,(dimethylaminocarbonyl)methyloxy, amino, methylamino, dimethylamino,diethylamino, acetylamino, methylsulfonylamino, methylthio,methylsulfonyl, methylsulfinyl, aminosulfonyl, methylaminosulfonyl anddimethylaminosulfonyl.

[1448] Examples of C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to5 substituent(s) selected from group D include benzyl, 1-naphthylmethyl,2-naphthylmethyl, phenethyl, 3-phenylpropyl, 2-phenylpropyl,3-fluorobenzyl, 4-fluorobenzyl, 3-chlorobenzyl, 4-chlorobenzyl,2,4-dichlorobenzyl, 3,5-dichlorobenzyl, 4-bromobenzyl, 4-nitrobenzyl,pentafluorobenzyl, 4-methylbenzyl, 4-tert-butylbenzyl,2-trifluoromethylbenzyl, 4-trifluoromethylbenzyl,4-(hydroxymethyl)benzyl, 4-(methoxymethyl)benzyl,4-(2-carboxylethyl)benzyl, 3-carboxylbenzyl, 4-carboxylbenzyl,4-methoxybenzyl, 3,4,5-trimethoxybenzyl, 4-carbamoylbenzyl,4-methylthiobenzyl, 4-(dimethylaminocarbonyl)benzyl,4-methylsulfonylbenzyl, 4-(acetylamino)benzyl, 4-cyanobenzyl,4-acetylbenzyl, 4-aminobenzyl, 4-dimethylaminobenzyl,4-(methylsulfonylamino)benzyl, 4-methylsulfinylbenzyl,4-aminosulfonylbenzyl, (3-nitro-4-methoxyphenyl)methyl and(4-nitro-3-methoxyphenyl)methyl.

[1449] At Z and Z′, the C₆₋₁₄ aryl C₁₋₆ alkyl moiety is preferablybenzyl or phenethyl, and the group D here is preferably theabove-defined halogen atom, nitro, the above-defined optionallysubstituted C₁₋₆ alkyl, —(CH₂)_(t)—COOR^(a19),—(CH₂)_(t)—CONR^(a27)R^(a23), —(CH₂)_(t)—OR^(a20),—(CH₂)_(t)—NR^(a29)CO—R^(a24), —(CH₂)_(t)—S(O)_(q)—R^(a25) or—(CH₂)_(t)—SO₂—NHR^(a26).

[1450] The C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from group D is preferably benzyl,3-fluorobenzyl, 4-fluorobenzyl, 3-chlorobenzyl, 4-chlorobenzyl,3,5-dichlorobenzyl, 4-bromobenzyl, 4-nitrobenzyl, 4-methylbenzyl,4-tert-butylbenzyl, 2-trifluoromethylbenzyl, 4-trifluoromethylbenzyl,4-(hydroxymethyl)benzyl, 4-(methoxymethyl)benzyl,4-(2-carboxylethyl)benzyl, 3-carboxylbenzyl, 4-carboxylbenzyl,4-methoxybenzyl, 3,4,5-trimethoxybenzyl, 4-carbamoylbenzyl,4-methylthiobenzyl, 4-(dimethylaminocarbonyl)benzyl,4-methylsulfonylbenzyl, 4-acetylaminobenzyl, 4-methylsulfinylbenzyl or4-aminosulfonylbenzyl.

[1451] It is particularly preferably the above-defined halogen atom, theabove-defined optionally substituted C₁₋₆ alkyl, —(CH₂)_(t)—COOR^(a19),—(CH₂)_(t)—CONR^(a27)R^(a28), —(CH₂)_(t)—OR^(a20) or—(CH₂)_(t)—S(O)_(q)—R^(a25) Examples thereof include fluorine atom,chlorine atom, bromine atom, nitro, methyl, tert-butyl, carboxyl,trifluoromethyl, hydroxymethyl, methoxymethyl, 2-carboxylethyl, methoxy,carbamoyl, methylthio, dimethylaminocarbonyl, methylsulfonyl andacetylamino. It is more preferably fluorine atom, chlorine atom, methyl,tert-butyl, carboxyl, methoxy, carbamoyl, methylthio,dimethylaminocarbonyl or methylsulfonyl, most preferably fluorine atomor chlorine atom.

[1452] The heterocycle C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from group B is that wherein the above-definedheterocycle C₁₋₆ alkyl is optionally substituted by 1 to 5substituent(s), and includes unsubstituted heterocycle C₁₋₆ alkyl. Thesubstituent(s) is(are) selected from the above-mentioned group B.

[1453] Examples thereof include 2-pyridylmethyl, 3-pyridylmethyl,2-chloropyridin-4-ylmethyl, 4-pyridylmethyl, pyrrolylmethyl,imidazolylmethyl, 2-thienylmethyl, 3-thienylmethyl, 2-furylmethyl,2-oxazolylmethyl, 5-isothiazolylmethyl, 2-methyloxazol-4-ylmethyl,2-thiazolylmethyl, 4-thiazolylmethyl, 5-thiazolylmethyl,2-methylthiazol-4-ylmethyl, 2-methylthiazol-5-ylmethyl,2,5-dimethylthiazol-4-ylmethyl, 4-methylthiazol-2-ylmethyl,2,4-dimethylthiazol-5-ylmethyl, 2-isothiazolylmethyl,2-pyrrolinylmethyl, pyrrolidinylmethyl, piperidylmethyl,4-piperidylmethyl, 1-methylpiperidin-4-ylmethyl,4-hydroxypiperidinomethyl, 3-hydroxypyrrolidinylmethyl,2-(4-hydroxypiperidino)ethyl,1-(tert-butoxycarbonyl)piperidin-4-ylmethyl,1-acetylpiperidin-4-ylmethyl, 1-methylsulfonylpiperidin-4-ylmethyl,piperazinylmethyl, morpholinomethyl, thiomorpholinylmethyl,1-tetrahydropyranylmethyl, 2-quinolylmethyl, 1-isoquinolylmethyl and thelike.

[1454] The heterocyclic moiety is preferably a heterocyclic group whichis a 5-membered or 6-membered monocyclic group. Examples thereof includepyridyl, pyrazinyl, pyrimidinyl, pyridazinyl, 1,3,5-triazinyl, pyrrolyl,pyrazolyl, imidazolyl, 1,2,4-triazolyl, tetrazolyl, thienyl, furyl,oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, thiadiazolyl,pyrrolidinyl, piperidyl, piperazinyl, morpholinyl, thiomorpholinyl andtetrahydropyranyl, and the alkyl moiety thereof is preferably straightchain alkyl having 1 to 4 carbon atoms. The group B here is preferablythe above-defined halogen atom, the above-defined C₁₋₆ alkyl, theabove-defined halogenated C₁₋₆ alkyl, the above-defined C₁₋₆ alkanoyl,(CH₂)_(r)—COOR^(b1), —(CH₂)_(r)CONR^(b1)R^(b2) or —(CH₂)_(r)—OR^(b1).

[1455] Examples of heterocycle C₁₋₆ alkyl optionally substituted by 1 to5 substituent(s) selected from group B preferably include2-pyridylmethyl, 3-pyridylmethyl, 2-chloropyridin-4-ylmethyl,4-pyridylmethyl, piperidin-4-ylmethyl, 1-methylpiperidin-4-ylmethyl,2-(4-hydroxypiperidino)ethyl, 1-acetylpiperidin-4-ylmethyl,1-(tert-butoxycarbonyl)piperidin-4-ylmethyl,1-(methylsulfonyl)-piperidin-4-ylmethyl, 2-thiazolylmethyl,4-thiazolylmethyl, 2-methylthiazolin-4-ylmethyl,2,4-dimethylthiazolin-5-ylmethyl and 4-methylthiazol-2-ylmethyl.Particularly preferably, it is 2-pyridylmethyl, 3-pyridylmethyl,2-chloropyridin-4-ylmethyl, 4-pyridylmethyl, piperidin-4-ylmethyl,1-methylpiperidin-4-ylmethyl, 2-(4-hydroxypiperidino)ethyl,1-acetylpiperidin-4-ylmethyl,1-(tert-butoxycarbonyl)piperidin-4-ylmethyl,1-(methylsulfonyl)piperidin-4-ylmethyl, 2-methylthiazolin-4-ylmethyl,2,4-dimethylthiazolin-5-ylmethyl or 4-methylthiazol-2-ylmethyl atR^(a20), 2-pyridylmethyl at R^(a22) and R^(a23), and 4-pyridylmethyl or4-methylthiazol-2-ylmethyl at R^(a27) and R^(a28).

[1456] The heterocycle C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from group D is that wherein the above-definedheterocycle C₁₋₆ alkyl is optionally substituted by 1 to 5substituent(s), and includes unsubstituted heterocycle C₁₋₆ alkyl. Thesubstituent(s) is(are) selected from the above-mentioned group D(substituents shown under (a) to (q)).

[1457] Examples of group D here include fluorine atom, chlorine atom,bromine atom, nitro, cyano, methyl, ethyl, propyl, isopropyl,tert-butyl, trifluoromethyl, hydroxymethyl, 2-hydroxyethyl,methoxymethyl, 2-carboxylethyl, methoxycarbonylmethyl,ethoxycarbonylmethyl, acetyl, carboxyl, methoxycarbonyl, ethoxycarbonyl,carbamoyl, methylaminocarbonyl, isopropylaminocarbonyl,dimethylaminocarbonyl, diethylaminocarbonyl,(2-hydroxyethyl)aminocarbonyl, (carboxylmethyl)aminocarbonyl, hydroxylgroup, methoxy, ethoxy, isopropyloxy, hydroxymethyloxy,carboxylmethyloxy, (dimethylaminocarbonyl)methyloxy, amino, methylamino,dimethylamino, diethylamino, acetylamino, methylsulfonylamino,methylthio, methylsulfonyl, methylsulfinyl, aminosulfonyl,methylaminosulfonyl and dimethylaminosulfonyl.

[1458] Examples of heterocycle C₁₋₆ alkyl optionally substituted by 1 to5 substituent(s) selected from group D include 2-pyridylmethyl,3-pyridylmethyl, 2-chloropyridin-4-ylmethyl, 4-pyridylmethyl,pyrrolylmethyl, imidazolylmethyl, 2-thienylmethyl, 3-thienylmethyl,2-furylmethyl, 2-oxazolylmethyl, 5-isothiazolylmethyl,2-methyloxazol-4-ylmethyl, 2-thiazolylmethyl, 4-thiazolylmethyl,5-thiazolylmethyl, 2-methylthiazol-4-ylmethyl,2-methylthiazol-5-ylmethyl, 2,5-dimethylthiazol-4-ylmethyl,4-methylthiazol-2-ylmethyl, 2,4-dimethylthiazol-5-ylmethyl,2-isothiazolylmethyl, 2-pyrrolinylmethyl, pyrrolidinylmethyl,piperidylmethyl, 4-piperidylmethyl, 1-methylpiperidin-4-ylmethyl,4-hydroxypiperidinomethyl, 2-(4-hydroxypiperidino)ethyl,1-(tert-butoxycarbonyl)piperidin-4-ylmethyl,1-acetylpiperidin-4-ylmethyl, 1-methylsulfonylpiperidin-4-ylmethyl,piperazinylmethyl, morpholinomethyl, thiomorpholinylmethyl,1-tetrahydropyranylmethyl, 2-quinolylmethyl, 1-isoquinolylmethyl, andthe like.

[1459] Preferable heterocyclic moiety at Z and Z′ is heterocylic groupwhich is 5-membered or 6-membered monocyclic group. Examples of theheterocyclic moiety include pyridyl, pyrazinyl, pyrimidinyl,pyridazinyl, 1,3,5-triazinyl, pyrrolyl, pyrazolyl, imidazolyl,1,2,4-triazolyl, tetrazolyl, thienyl, furyl, oxazolyl, isooxazolyl,thiazolyl, isothiazolyl, thiadiazolyl, pyrrolidinyl, piperidyl,piperazinyl, morpholinyl, thiomorpholinyl and tetrahydropyranyl, and thealkyl moiety is preferably straight chain alkyl having 1 to 4 carbonatoms, particularly methyl (i.e., methylene).

[1460] Preferable group D is the above-defined halogen atom, nitro, theabove-defined optionally substituted C₁₋₆ alkyl, —(CH₂)_(t)—COOR^(a19),—(CH₂)_(t)—CONR^(a27)R^(a28), —(CH₂)_(t)—OR^(a20),—(CH₂)_(t)NR^(a29)CO—R^(a24), —(CH₂)_(t)—S(O)_(q)—R^(a25) or—(CH₂)_(t)—SO₂—NHR^(a26).

[1461] Preferable examples of heterocycle C₁₋₆ alkyl optionallysubstituted by 1 to 5 substituent(s) selected from group D include2-pyridylmethyl, 3-pyridylmethyl, 2-chloropyridin-4-ylmethyl,4-pyridylmethyl, piperidin-4-ylmethyl, 1-methylpiperidin-4-ylmethyl,4-hydroxypiperidinomethyl, 2-(4-hydroxypiperidino)ethyl,1-acetylpiperidin-4-ylmethyl,1-(tert-butoxycarbonyl)piperidin-4-ylmethyl,1-(methylsulfonyl)piperidin-4-ylmethyl, 2-thiazolylmethyl,4-thiazolylmethyl, 2-methylthiazolin-4-ylmethyl,2,4-dimethylthiazolin-5-ylmethyl and 4-methylthiazol-2-ylmethyl.

[1462] Particularly preferred is 4-hydroxypiperidinomelthyl.

[1463] The C₃₋₈ cycloalkyl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B is that wherein theabove-defined C₃₋₈ cycloalkyl C₁₋₆ alkyl is optionally substituted by 1to 5 substituent(s), and includes unsubstituted cycloalkylalkyl. Thesubstituents are selected from the above group B.

[1464] Specific examples thereof include cyclopropylmethyl,cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl,2-(cyclopentyl)ethyl, 2-(cyclohexyl)ethyl, cycloheptylmethyl,4-fluorocyclohexylmethyl, 2-methylcyclopentylmethyl,3-methylcyclohexylmethyl, 4-methylcyclohexylmethyl,4,4-dimethylcyclohexylmethyl, 3,5-dimethylcyclohexylmethyl,4-tert-butylcyclohexylmethyl, 4-hydroxycyclohexylmethyl,4-methoxycyclohexylmethyl and 2,3,4,5,6-pentafluorocyclohexylmethyl.

[1465] Also exemplified are those wherein cyclopentylmethyl orcyclohexylmethyl is substituted by fluorine atom, chlorine atom, bromineatom, nito, methyl, tert-butyl, carboxyl, trifluoromethyl,hydroxymethyl, methoxymethyl, 2-carboxylethyl, methoxy, carbamoyl,methylthio, dimethylaminocarbonyl, methylsulfonyl or acetylamino.

[1466] At cycloalkyl moiety, it is preferably cyclopentylmethyl orcyclohexylmethyl, and at R^(a20), R^(a27) and R^(a28), it isparticularly preferably cyclohexylmethyl.

[1467] The carboxyl-protecting group only needs to be suitable forreaction conditions, and is capable of protecting and deprotecting andmay be, for example, methyl; substituted methyl group such asmethoxymethyl, methylthiomethyl, 2-tetrahydropyranyl,methoxyethoxymethyl, benzyloxymethyl, phenacyl, diacylmethyl,phthalimidomethyl etc.; ethyl; substituted ethyl group such as2,2,2-trichloroethyl, 2-chloroethyl, 2-(trimethylsilyl)ethyl,2-methylthioethyl, 2-(p-toluenesulfonyl)ethyl, t-butyl etc.; benzyl;substituted benzyl group such as diphenylmethyl, triphenylmethyl,p-nitrobenzyl, 4-picolyl, p-methoxybenzyl, 2-(9,10-dioxo)anthrylmethyl(etc.; silyl group such as trimethylsilyl, t-butyldimethylsilyl,phenyldimethylsilyl etc.; and the like.

[1468] Preferred are industrially effective protecting groups andspecifically preferred as R^(a36) are methyl and ethyl.

[1469] In formula [I], X is preferably

[1470] wherein each symbol is as defined above.

[1471] G¹, G², G³ and G⁴ are each preferably (C—R¹), (C—R²) (C—R³) and(C—R⁴), G⁵ is preferably a nitrogen atom, and G⁶, G⁸, and G⁹ arepreferably a carbon atom. G⁷ is preferably C(—R⁷) or unsubstitutednitrogen atom, wherein R⁷ is preferably hydrogen atom.

[1472] A preferable combination is G² of (C—R²) and G⁶ of a carbon atom,particularly preferably G² of (C—R²), G⁶ of a carbon atom and G⁵ of anitrogen atom, most preferably G² of (C—R²), G⁶ of a carbon atom, G⁵ ofa nitrogen atom and G⁷ of unsubstituted nitrogen atom.

[1473] In formulas [I] and [II], 1 to 4 of G¹ to G⁹ in the moiety

[1474] is(are) preferably a nitrogen atom, specifically preferably

[1475] particularly preferably

[1476] more preferably

[1477] most preferably

[1478] It is also a preferable embodiment wherein the

[1479] moiety is aromatic ring.

[1480] R¹ and R⁴ are preferably hydrogen atom. R² is preferablycarboxyl, —COOR^(a1), —CONR^(a2)R^(a3), —SO₂R^(a7) (each symbol is asdefined above) or heterocyclic group having 1 to 4 heteroatom(s)selected from an oxygen atom, a nitrogen atom and a sulfur atom,particularly preferably carboxyl, —COOR^(a1) or —SO₂R^(a7), morepreferably carboxyl or —COOR^(a1), most preferably carboxyl. R³ ispreferably hydrogen atom or —OR^(a6) (R^(a6) is as defined above),particularly preferably hydrogen atom.

[1481] R^(a1) is preferably optionally substituted C₁₋₆ alkyl.

[1482] When R² is carboxyl or —COOR^(a1), at least one of R¹, R³ and R⁴is preferably hydroxyl group, halogen atom (particularly fluorine atom,chlorine atom) or —OR^(a6) (wherein R^(a6) is preferably hydrogen atomor methyl).

[1483] The ring Cy and ring Cy′ are preferably cyclopentyl, cyclohexyl,cycloheptyl, tetrahydrothiopyranyl or piperidino, particularlypreferably cyclopentyl, cyclohexyl or cycloheptyl, more preferablycyclohexyl.

[1484] The ring A and ring A′ are preferably phenyl, pyridyl, pyrazinyl,pyrimidinyl, pyridazinyl, cyclohexyl, cyclohexenyl, furyl or thienyl,particularly preferably phenyl, pyridyl, pyrazinyl, pyrimidinyl orpyridazinyl, more preferably phenyl or pyridyl, and most preferablyphenyl.

[1485] The ring B and ring B′ are preferably C₁₋₆ aryl or heterocyclicgroup, specifically preferably, phenyl, pyridyl, pyrazinyl, pyrimidinyl,pyridazinyl, 1,3,5-triazinyl, pyrrolyl, pyrazolyl, imidazolyl,1,2,4-triazolyl, tetrazolyl, thienyl, furyl, oxazolyl, isoxazolyl,thiazolyl, isothiazolyl or thiadiazolyl, particularly preferably phenyl,pyridyl, pyrimidinyl, 1,3,5-triazinyl or thiazolyl, more preferably,phenyl, pyridyl or thiazolyl, and most preferably phenyl or thiazolyl.

[1486] With regard to R⁵ and R⁶, one of them is preferably hydrogen atomand the other is halogen atom, particularly fluorine atom.Alternatively, the both are preferably hydrogen atoms. When ring A isphenyl, R⁵ and R⁶ preferably are present at an ortho position from G⁶.The same applies to R⁵′ and R⁶′.

[1487] Y is preferably —(CH₂)_(m)—O—(CH₂)_(n)—, —NHCO₂—,—CONH—CHR^(a14)—, —(CH₂)_(m)NR^(a12)—(CH₂)_(n)—, —CONR^(a13)—(CH₂)_(n)—,—O—(CH₂)_(m)—CR^(a15)R^(a16)—(CH₂)_(n)— or—(CH₂)_(n)—NR^(a12)—CHR^(a15)— (each symbol is as defined above), morepreferably, —(CH₂)_(m)—O—(CH₂)_(n)— or—O—(CH₂)_(m)—CR^(a15)R^(a16)—(CH₂)_(n)—, most preferably—O—(CH₂)_(m)—CR^(a15)R^(a16)—(CH₂)_(n)—. The l, m and n are preferably 0or an integer of 1 to 4, particularly preferably 0, 1 or 2, at Y. In—(CH₂)_(m)—O—(CH₂)_(n)—, m=n=0 or m=0 and n=1 is more preferable, mostpreferably m=n=0. In —O—(CH₂)_(m)—CR^(a15)R^(a16)—(CH₂)_(n)—, m=n=0, m=0and n=1, m=1 and n=0 or m=1 and n=1 is more preferable, most preferablym=n=0.

[1488] When Y is —O—(CH₂)_(m)—CR^(a15)R^(a16)—(CH₂)_(n)—, R^(a16) ispreferably hydrogen atom, R^(a15) is preferably

[1489] wherein the

[1490] moiety is preferably symmetric. The preferable mode of n, ring B,Z and w and the preferable mode of n′, ring B′, Z′ and w′ are the same.

[1491] When ring A is phenyl, X or Y is preferably present at thepara-position relative to G⁶. When ring B and ring B′ are phenyl, Z ispreferably present at the ortho or meta-position relative to Y. It ispreferable that the 3-position on phenyl have one substituent or the2-position and the 5-position on phenyl each have one substituent.

[1492] When ring B is thiazolyl, Y is preferably substituted at the5-position, and Z is preferably substituted at the 2-position, the4-position or the 2-position and the 4-position. similarly, when ring B′is thiazolyl, (CH₂)_(n)—, is also preferably substituted at the5-position, and Z′ is preferably substituted at the 2-position, the4-position or the 2-position and the 4-position.

[1493] Z and Z′ are preferably group D, “C₆₋₁₄ aryl optionallysubstituted by 1 to 5 substituent(s) selected from group D” or“heterocyclic group optionally substituted by 1 to 5 substituent(s)selected from group D”, particularly preferably group D or “C₆₋₁₄ aryloptionally substituted by 1 to 5 substituent(s) selected from group D”.

[1494] More preferably, they are the above-defined halogen atom, nitro,the above-defined optionally substituted C₁6 alkyl, —(CH₂)_(t)—COOR ,—(CH₂)_(t)—CONR^(a27)R^(a28), —(CH₂)_(t)—OR^(a20),—(CH₂)_(t)—R^(a29)CO—R^(a24), —(CH₂)_(t)—S(O)_(q)—R^(a25) or—(CH₂)_(t)—SO₂—NHR^(a26), or C₆₋₁₄ aryl or heterocyclic group optionallysubstituted by these.

[1495] With regard to Z and Z′, the preferable mode of group D thatdirectly substitutes each ring B and ring B′ and the preferable mode ofgroup D that substitutes C₆₋₁₄ aryl, C₃₋₈ cycloalkyl, C₆₋₁₄ aryl C₁₋₆alkyl or heterocyclic group are the same, wherein they may be the samewith or different from each other.

[1496] Specific examples of the substituent preferably include fluorineatom, chlorine atom, bromine atom, nitro, cyano, methyl, ethyl, propyl,isopropyl, tert-butyl, trifluoromethyl, hydroxymethyl, 2-hydroxyethyl,methoxymethyl, 2-carboxylethyl, methoxycarbonylmethyl,ethoxycarbonylmethyl, carbamoylmethoxymethyl,(dimethylaminocarbonyl)methoxymethyl, acetyl, isovaleryl, carboxyl,methoxycarbonyl, ethoxycarbonyl, carbamoyl, methylaminocarbonyl,hydroxyaminocarbonyl, ethylaminocarbonyl, propylaminocarbonyl,isopropylaminocarbonyl, butylaminocarbonyl, isobutylaminocarbonyl,tert-butylaminocarbonyl, (4-hydroxybutyl)aminocarbonyl,(1-hydroxypropan-2-yl)aminocarbonyl,(2,3-dihydroxypropyl)-aminocarbonyl,(1,3-dihydroxypropan-2-yl)aminocarbonyl, methoxyaminocarbonyl,{2-[2-(methoxy)ethoxy]ethyl}aminocarbonyl,N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylaminocarbonyl,N-isopropyl-N-methylaminocarbonyl, dimethylaminocarbonyl,diethylaminocarbonyl, (2-hydroxyethyl)aminocarbonyl,(2-hydroxy-2-methylpropan-2-yl)aminocarbonyl,(carboxylmethyl)aminocarbonyl, hydroxyl group, methoxy, ethoxy,propyloxy, isopropyloxy, butyloxy, isopentyloxy, 2-isopentenyloxy,3-isohexenyloxy, 4-methyl-3-pentenyloxy, 2-propynyloxy,trifluoromethyloxy, hydroxymethyloxy, carboxylmethyloxy,(dimethylaminocarlbonyl)-methyloxy, amino, methylamino, dimethylamino,diethylamino, acetylamino, N-acetyl-N-methylamino, ureido,isopropylcarbonylamino, isobutylcarbonylamino, tert-butylcarbonylamido,(ethylamino)carbonylamino, (isopropylamino)-carbonylamino,(dimethylamino)carbonylamino, (4-hydroxypiperidino)carbonylamino,[(4-hydroxypiperidinolmethyl]-carbonylamino,[(3-hydroxypyrrolidinyl)methyl]carbonylamino, methylsulfonylamino,isopropylsulfonylamino, N-(isopropylsulfonyl)-N-methylamino, methylthio,methylsulfonyl, isopropylsulfonyl, isobutylsulfonyl, methylsulfinyl,isopropylsulfinyl, aminosulfonyl, methylaminosulfonyl,dimethylaminosulfonyl, isopropylaminosulfonyl, tert-butylamino-sulfonyl,hydroxyamidino, phenyl, 3-fluorophenyl, 4-fluorophenyl, 3-chlorophenyl,4-chlorophenyl, 2,4-difluorophenyl, 3,4-difluorophenyl,3,4-dichlorophenyl, 3,5-dichlorophenyl, 4-chloro-3-fluorophenyl,4-chloro-2-fluorophenyl, 4-bromophenyl, 4-nitrophenyl, 4-cyanophenyl,4-methylphenyl, 4-ethylphenyl, 4-propylphenyl, 4-isopropylphenyl,4-tert-butylphenyl, 2-trifluoromethylphenyl, 4-trifluoromethylphenyl,4-(hydroxymethyl)phenyl, 4-(2-hydroxyethyl)phenyl,4-(methoxymethyl)phenyl, 4-(2-carboxylethyl)phenyl,4-(methoxycarbonylmethyl)phenyl, 4-(ethoxycarbonylmethyl)phenyl,4-acetylphenyl, 3-carboxylphenyl, 4-carboxylphenyl,4-(methoxycarbonyl)phenyl, 4-(ethoxycarbonyl)phenyl, 4-carbamoylphenyl,4-(methylaminocarbonyl)phenyl, 4-(isopropylaminocarbonyl)phenyl,4-(dimethylaminocarbonyl)phenyl, 4-(diethylaminocarbonyl)phenyl,4-[(2-hydroxyethyl)-aminocarbonyl]phenyl,4-[(carboxylmethyl)aminocarbonyl]phenyl, 4-hydroxyphenyl,4-methoxyphenyl, 3,4,5-trimethoxyphenyl, 4-ethoxyphenyl,4-propyloxyphenyl, 4-isopropyloxyphenyl, 4-butyloxyphenyl,4-isopentyloxyphenyl, 4-(2-isopentenyloxy)phenyl,4-(3-isohexenyloxy)phenyl, 4-(4-methyl-3-pentenyloxy)phenyl,4-(2-propynyloxy)phenyl, 4-(trifluoromethyloxy)phenyl,4-(hydroxymethyloxy)phenyl, 4-(carboxylmethyloxy)phenyl,4-[(dimethylaminocarbonyl)methyloxy]phenyl, 4-aminophenyl,4-(methylamino)phenyl, 4-(dimethylaminophenyl), 4-(diethylamino)-phenyl,4-(acetylamino)phenyl, 4-(methylsulfonylamino)-phenyl,4-(methylthio)phenyl, 4-(methylsulfonyl)phenyl,4-(methylsulfinyl)phenyl, 4-(aminosulfonyl)phenyl,4-(methylaminosulfonyl)phenyl, 4-(dimethylaminosulfonyl)-phenyl,4-(tert-butylaminosulfonyl)phenyl, tetrazol-5-ylphenyl, cyclohexyl,benzyl, 4-chlorobenzyl, phenethyl, benzyloxy, 4-fluorobenzyloxy,2-chlorobenzyloxy, 3-chlorobenzyloxy, 4-chlorobenzyloxy,4-tert-butylbenzyloxy, 4-trifluoromethylbenzyloxy, phenethyloxy,2-thienyl, 2-thiazolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl,6-fluoropyridin-3-yl, 5-fluoropyridin-2-yl, 6-chloropyridin-3-yl,6-methylpyridin-3-yl, 2-pyrimidinyl, 5-tetrazolyl, piperidino,2-oxopiperidin-1-yl, 2-oxopyrrolidin-1-yl, 2-imidazolin-2-yl,2-oxoimidazolidin-1-yl, 2-oxooxazolidin-1-yl, 2-methylthiazol-4-yl,5-methylthiazol-2-yl, 2-aminothiazol-4-yl,3-methyl-1,2,4-oxadiazol-5-yl, 1,1-dioxoisothiazolidin-2-yl,4,4-dimethyl-Δ²-oxazolin-2-yl, 5-chlorothiophen-2-yl,5-methyloxazol-2-yl, 5-oxo-Δ²-1,2,4-oxadiazolin-3-yl,5-oxo-Δ²-1,2,4-thiadiazolin-3-yl, 2-oxo-3H-1,2,3,5-oxathiadiazolin-4-yl,4-hydroxypiperidinomethyl, piperidinocarbonyl,4-hydroxypiperidinocarbonyl, 3,4-dihydroxypiperidinocarbonyl,1-piperazinylcarbonyl, 1-pyrrolidinylcarbonyl, morpholinocarbonyl,4-thiomorpholinylcarbonyl, phenoxy, 2,4-dichlorophenoxy,tetrahydropyranyloxy, 2-pyridylmethyloxy, 3-pyridylmethyloxy,2-chloropyridin-4-ylmethyloxy, 4-pyridylmethyloxy, 2-piperidylmethyloxy,3-piperidylmethyloxy, 4-piperidylmethyloxy,1-methylpiperidin-4-ylmethyloxy, 1-acetylpiperidin-4-ylmethyloxy,1-(tert-butoxycarbonyl)piperidin-4-ylmethyloxy,1-(methylsulfonyl)piperidin-4-ylmethyloxy, 2-methylthiazolin-4-yloxy,2,4-dimethylthiazolin-5-yloxy, dimethylaminocarbonyl-methyloxy,piperidinocarbonylmethyloxy, 4-hydroxypiperidino-carbonylmethyloxy,2-methylthiazol-4-yl, (2-methylthiazol-4-yl)methyloxy,(2,4-dimethylthiazol-5-yl)methyloxy, benzoyl, 3-fluorobenzoyl,4-chlorobenzylamino, 3,5-dichlorobenzylamino,4-trifluoromethylbenzylamino, 2-pyridylmethylamino, benzoylamino,4-chlorobenzoylamino, 4-trifluoromethylbenzoylamino,3,5-dichlorobenzoylamino, 3-nitro-4-methoxybenzoylamino,4-nitro-3-methoxybenzoylamino, 3-pyridylcarbonylamino,morpholinocarbonylamino, 2-oxazolinylamino, 4-hydroxypiperidinosulfony,1-methylphenylsulfonylamino, 2-thiazolylaminosulfonyl,2-pyridylaminosulfonyl, benzylaminocarbonyl,N-benzyl-N-methylaminocarbonyl, (4-pyridylmethyl)aminocarbonyl or(cyclohexylmethyl)aminocarbonyl, 2-hydroxyethyloxy, 3-hydroxypropyloxy,2-methoxyethoxy, 2-(2-methoxyethoxy) ethoxy, azetidinylcarbonyl,3-hydroxypyrrolidinylcarbonyl, 3-hydroxypiperidinocarbonyl,4-hydroxypiperidinocarbonyl, 3,4-dihydroxypiperidinocarbonyl,4-methoxypiperidinocarbonyl, 4-carboxypiperidinocarbonyl,4-(hydroxymethyl)piperidinocarbonyl, 2-oxopiperidinocarbonyl,4-oxopiperidinocarbonyl, 2,6-dimethylpiperidinocarbonyl,2,2,6,6-tetramethylpiperidinocarbonyl,2,2,6,6-tetramethyl-4-hydroxypiperidinocarbonyl,1-oxothiomorpholin-4-ylcarbonyl, 1,1-dioxothiomorpholin-4-ylcarbonyl,1-(methylsulfonyl)piperidin-4-ylaminocarbonyl,4-methylsulfonylpiperazinylcarbonyl, 4-methylpiperazinylcarbonyl,N,N-bis(2-hydroxyethyl)aminocarbonyl, phenylaminocarbonyl,cyclopropylaminocarbonyl, cyclobutylaminocarbonyl,cyclohexylaminocarbonyl, 4-hydroxycyclohexylaminocarbonyl,4-methylthiazol-2-ylmethylaminocarbonyl,2-(4-hydroxypiperidino)-ethyloxy, 2-pyridylmethylaminocarbonyl,3-pyridylmethylaminocarbonyl, N-methyl-N-(4-pyridylmethyl)aminocarbonyl,cyclohexylmethyloxy, 4-hydroxypiperidinocarbonylmethyloxy and4-methylthiazol-2-ylmethyloxy.

[1497] Particularly preferable examples of the substituent includefluorine atom, chlorine atom, bromine atom, nitro, cyano, methyl,hydroxymethyl, carboxyl, carbamoyl, methylaminocarbonyl,isopropylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl,(2-hydroxylethyl)aminocarbonyl, (carboxymethyl)-aminocarbonyl, methoxy,2-isopentenyloxy, 2-propynyloxy, methylthio, methylamino, dimethylamino,acetylamino, methylsulfonylamino, methylsulfonyl, aminosulfonyl,dimethylaminosulfonyl, tert-butylaminosulfonyl, phenyl, 3-fluorophenyl,4-fluorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,5-dichlorophenyl,4-nitrophenyl, 4-methylphenyl, 4-tert-butylphenyl,4-trifluoromethylphenyl, 4-(methoxymethyl phenyl,4-(2-hydroxylethyl)phenyl, 3-carboxylphenyl, 4-carboxylphenyl,4-methoxyphenyl, 4-carbamoylphenyl, 4-methylthiophenyl,4-(dimethylaminocarbonyl)phenyl, 4-methylsulfonylphenyl, benzyl,phenethyl, benzyloxy, 4-fluorobenzyloxy, 4-chlorobenzyloxy, 2-thiazolyl,3-pyridyl, 4-pyridyl, 4-pyridylmethyloxy, 2.-piperidylmethyloxy,3-piperidylmethyloxy, 4-piperidylmethyloxy,1-methylpiperidin-4-ylmethyloxy, 1-acetylpiperidin-4-ylmethyloxy,2-chloropiperidin-4-ylmethyloxy,1-(methylsulfonyl)piperidin-4-ylmethyloxy, 2-methylthiazol-4-yl,(2-methylthiazol-4-yl)methyloxy, (2,4-dimethylthiazol-5-yl)methyloxy,5-tetrazolyl, 3-fluorobenzoyl, piperidinocarbonyl,4-hydroxylpiperidinocarbonyl, 1-pyrrolidinylcarbonyl,morpholinocarbonyl, 4-thiomorpholinylcarbonyl, benzylaminocarbonyl,N-benzyl-N-methylaminocarbonyl, (4-pyridylmethyl)aminocarbonyl and(cyclohexylmethyl)aminocarbonyl.

[1498] Most preferable substituents are fluorine atom, chlorine atom,methyl, hydroxymethyl, carboxyl, carbamoyl, methylaminocarbonyl,dimethylaminocarbonyl, methoxy, methylamino, acetylamino, aminosulfonyl,dimethylaminosulfonyl, tert-butylaminosulfonyl, phenyl, 3-fluorophenyl,4-fluorophenyl, 3-chlorophenyl, 4-chlorophenyl, 3,5-dichlorophenyl,4-methylphenyl, 4-tert-butylphenyl, 4-trifluoromethylphenyl,4-carboxylphenyl, 4-methoxyphenyl, 4-carbamoylphenyl,4-methylthiophenyl, 4-(dimethylaminocarbonyl)phenyl,4-methylsulfonylphenyl and 2-oxopyrrolidin-1-yl.

[1499] The w is preferably 1 or 2, r and t are preferably 0, 1 or 2,particularly preferably 0 or 1, more preferably 0, )p is preferably 1,and q is preferably 0 or 2.

[1500] In formula [I], when X is

[1501] wherein each symbol is as defined above and w is 2 or above, oneof Z is preferably C₆₋₁₄ aryl optionally substituted by 1 to 5substituent(s) selected from group D or heterocyclic group optionallysubstituted by 1 to 5 substituent(s) selected from group D, particularlypreferably C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from group D.

[1502] The pharmaceutically acceptable salt may be any as long as itforms a non-toxic salt with a compound of the above-mentioned formula[I] or [II]. Such salt can be obtained by reacting the compound with aninorganic acid, such as hydrochloric acid, sulfuric acid, phosphoricacid, hydrobromic acid and the like, or an organic acid, such as oxalicacid, malonic acid, citric acid, fumaric acid, lactic acid, malic acid,succinic acid, tartaric acid, acetic acid, trifluoroacetic acid,gluconic acid, ascorbic acid, methylsulfonic acid, benzylsulfonic acidand the like, or an inorganic base, such as sodium hydroxide, potassiumhydroxide, calcium hydroxide, magnesium hydroxide, ammonium hydroxideand the like, or an organic base, such as methylamine, diethylamine,triethylamine, triethanolamine, ethylenediamine,tris(hydroxymethyl)methylamine, guanidine, choline, cinachonine and thelike, with an amino acid, such as lysine, arginine, alanine and thelike. The present invention encompasses water-retaining product, hydrateand solvate of each compound.

[1503] The compounds of the above-mentioned formula [I] or [II] havevarious isomers. For example, E compound and Z compound are present asgeometric isomers, and when the compound has an asymmetric carbon, anenantiomer and a diastereomer are present due to the asymmetric carbon.A tautomer may be also present. The present invention encompasses all ofthese isomers and mixtures thereof.

[1504] The present invention also encompasses prodrug and metabolite ofeach compound.

[1505] A prodrug means a derivative of the compound of the presentinvention, which is capable of chemical or metabolic decomposition,which shows inherent efficacy by reverting to the original compoundafter administration to a body, and which includes salts and complexeswithout a covalent bond.

[1506] When the inventive compound is used as a pharmaceuticalpreparation, the inventive compound is generally admixed withpharmaceutically acceptable carriers, excipients, diluents, binders,disintegrators, stabilizers, preservatives, buffers, emulsifiers,aromatics, coloring agents, sweeteners, thickeners, correctives,solubilizers, and other additives such as water, vegetable oil, alcoholsuch as ethanol, benzyl alcohol and the like, polyethylene glycol,glycerol triacetate, gelatin, lactose, carbohydrate such as starch andthe like, magnesium stearate, talc, lanolin, petrolatum and the like,and prepared into a dosage form of tablets, pills, powders, granules,suppositories, injections, eye drops, liquids, capsules, troches,aerosols, elixirs, suspensions, emulsions, syrups and the like, whichcan be administered systemically or topically and orally orparenterally.

[1507] While the dose varies depending on the age, body weight, generalcondition, treatment effect, administration route and the like, it isfrom 0.1 mg to 1 g for an adult per dose, which is given one to severaltimes a day.

[1508] The prophylaxis of hepatitis C means, for example, administrationof a pharmaceutical agent to an individual found to carry an HCV by atest and the like but without a symptom of hepatitis C, or to anindividual who shows an improved disease state of hepatitis after atreatment of hepatitis C, but who still carries an HCV and is associatedwith a risk of recurrence of hepatitis.

[1509] Inasmuch as HCV is known to be a virus associated with manygenetic mutations, a compound effective for many genotypes is one of thepreferable modes. If a compound ensures high blood concentration whenadministered as a pharmaceutical agent to an animal infected with HCV,it is also one of the preferable modes. From these aspects, a compoundhaving high inhibitory activity on both HCV type 1a and type 1b and highblood concentration, such as2-{4-[2-(4-chlorophenyl)-5-(2-oxopyrrolidin-1-yl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride, is particularly preferable.

[1510] The fused ring compound of the formula [I] or [II] of the presentinvention can be administered to mammals inclusive of human for thepurpose of prevention or treatment of hepatitis C or inhibition ofhepatitis C virus polymerase. The fused ring compound of the presentinvention can be also administered to mammals inclusive of human alongwith at least one pharmaceutical agent (hereinafter combination drug)selected from an antiviral agent other than the compound of the formula[I], an antiinflammatory agent and an immunostimulant for the purpose ofprevention or treatment of hepatitis C or inhibition of hepatitis Cvirus polymerase. In the case of combined administration, the compoundof the present invention can be administered simultaneously with thecombination drug or administered at certain time intervals. In the caseof combined administration, a pharmaceutical composition containing thecompound of the present invention and a combination drug can beadministered. Alternatively, a pharmaceutical composition containing thecompound of the present invention and a pharmaceutical compositioncontaining a combination drug may be administered separately. Theadministration route may be the same or different.

[1511] In the case of a combined administration, the compound of thepresent invention can be administered once a day or several times a dayin a single dose of 0.1 mg to 1 g, or may be administered in a smallerdose. The combination drug can be administered in a dose generally usedfor the prevention or treatment of hepatitis C or in a smaller dose.

[1512] Examples of other antiviral agent include interferons (interferonα, interferon β, interferon γ etc.), Ribavirin(1-β-D-ribofuranosyl-1H-1,2,4-triazole-3-carboxamide) and the like.

[1513] Examples of the production method of the compound to be used forthe practice of the present invention are given in the following.However, the production method of the compound of the present inventionis not limited to these examples.

[1514] Even if no directly corresponding disclosure is found in thefollowing Production Methods, the steps may be modified for efficientproduction of the compound, such as introduction of a protecting groupinto a functional group with deprotection in a subsequent step, andchanging the order of Production Methods and steps.

[1515] The treatment after reaction in each step may be( conventionalones, for which typical methods, such as isolation and purification,crystallization, recrystallization, silica gel chromatography,preparative HPLC and the like, can be appropriately selected andcombined.

[1516] Production Method 1

[1517] In this Production Method, a benzimidazole compound is formedfrom a nitrobenzene compound.

[1518] Production Method 1-1

[1519] wherein Hal is halogen atom, such as chlorine atom, bromine atomand the like, R^(c1) is halogen atom, such as chlorine atom, bromineatom and the like, or hydroxyl group, and other symbols are as definedabove.

[1520] Step 1

[1521] A compound [1] obtained by a conventional method or acommercially available compound [1] is reacted with amine compound [2]in a solvent such as N,N-dimethylformamide (DMF), acetonitrile,tetrahydrofuran (THF), toluene and the like in the presence or absenceof a base such as potassium carbonate, triethylamine, potassiumt-butoxide and the like at room temperature or with heating to givecompound [3].

[1522] Step 2

[1523] The compound [3] is hydrogenated in a solvent such as methanol,ethanol, THF, ethyl acetate, acetic acid, water and the like in thepresence of a catalyst such as palladium carbon, palladium hydroxide,platinum oxide, Raney nickel and the like at room temperature or withheating to give compound [4]. In addition, compound [3] is reduced witha reducing agent such as zinc, iron, tin(II) chloride, sodium sulfiteand the like, or reacted with hydrazine in the presence of iron(III)chloride to give compound [4].

[1524] Step 3

[1525] The compound [4] is condensed with carboxylic acid compound [5]in a solvent such as DMF, acetonitrile, THF, chloroform, ethyl acetate,methylene chloride, toluene and the like using a condensing agent suchas dicyclohexylcarbodiimide,1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride,diphenylphosphoryl azide and the like and, where necessary, addingN-hydroxysuccinimide, 1-hydroxybenzotriazole and the like to give amidecompound [6]. Alternatively, amide compound [6] can be obtained fromcompound [5] as follows. The carboxylic acid compound [5] is convertedto an acid halide derived with thionyl chloride, oxalyl chloride and thelike, or an active ester (e.g., mixed acid anhydride derived with ethylchlorocarbonate and the like), which is then reacted in the presence ofa base, such as triethylamine, potassium carbonate, pyridine and thelike, or in an amine solvent, such as pyridine and the like, to giveamide compound [6].

[1526] Step 4

[1527] The compound [6] is heated in a solvent such as ethanol,methanol, toluene, DMF, chloroform and the like or without a solvent inthe presence of an acid such as acetic acid, formic acid, hydrochloricacid, dilute sulfuric acid, phosphoric acid, polyphosphoric acid,p-toluenesulfonic acid and the like, a halogenating agent such as zincchloride, phosphorus oxychloride, thionyl chloride and the like or acidanhydride such as acetic anhydride and the like, to allow cyclization togive compound [I-2].

[1528] Production Method 1-2

[1529] This Production Method is an alternative method for producingcompound [I-2].

[1530] wherein each symbol is as defined above.

[1531] Step 1

[1532] The compound [3] obtained in the same manner as in Step 1 ofProduction Method 1-1 is subjected to amide condensation with compound[5] in the same manner as in Step 3 of Production Method 1-1 to givecompound [7].

[1533] Step 2

[1534] The compound [7] is reduced in the same manner as in Step 2 ofProduction Method 1-1 to give compound [8].

[1535] Step 3

[1536] The compound [8] is subjected to cyclization in the same manneras in Step 4 of Production Method 1-1 to give compound [I-2].

[1537] Production Method 1-3

[1538] wherein R^(c2) is alkyl such as methyl, ethyl and the like, andother symbols are as defined above.

[1539] The compound [4] is reacted with imidate compound. [9] in asolvent such as methanol, ethanol, acetic acid, DMF, THF, chloroform andthe like at room temperature or with heating to give compound [I-2].

[1540] In addition, compound [4] may be reacted with aldehyde compound[10] in a solvent such as acetic acid, formic acid, acetonitrile, DMF,nitrobenzene, toluene and the like in the presence or absence of anoxidizing agent such as benzofuroxan, manganese dioxide,2,3-dichloro-5,6-dicyano-p-benzoquinone, iodine, potassium ferricyanideand the like with heating to give compound [I-2].

[1541] Alternatively, compound [4] and carboxylic acid compound [11] maybe heated to allow reaction in the presence of polyphosphoric acid,phosphoric acid, phosphorus oxychloride, hydrochloric acid and the liketo give compound [I-2].

[1542] Production Method 2

[1543] In this Production Method, conversion of the substituents (R¹,R², R³, R⁴) on the benzene ring of benzimidazole is shown. While amethod of converting R² when R¹, R³ and R⁴ are hydrogen atoms is shown,this Production Method is applicable irrespective of the position ofsubstitution.

[1544] Production Method 2-1

[1545] Conversion of Carboxylic Acid Ester Moiety to Amide

[1546] wherein E is a single bond, —(CH₂)_(s)—, —O—(CH₂)_(s)— or—NH—(CH₂)_(s)— (wherein s is an integer of 1 to 6), R^(c3), R^(c4) andR^(c5) are C₁₋₆alkyl, and other symbols are as defined above.

[1547] Step 1

[1548] The compound [I-2-1] obtained in the same manner as in theabove-mentioned Production Method is subjected to hydrolysis in asolvent such as methanol, ethanol, THF, dioxane and the like, or in amixed solvent of these solvents and water under basic conditions withsodium hydroxide, potassium hydroxide, potassium carbonate, lithiumhydroxide and the like or under acidic conditions with hydrochloricacid, sulfuric acid and the like to give compound [I-2-2].

[1549] Step 2

[1550] The compound [I-2-2] is reacted with compound [12] in the samemanner as in Step 3 of Production Method 1-1 to give compound [I-2-3].

[1551] Production Method 2-2

[1552] Conversion of Cyano Group to Substituted Amidino Group

[1553] wherein each symbol is as defined above.

[1554] The compound [I-2-4] obtained in the same manner as in theabove-mentioned Production Method is reacted with hydroxylamine in asolvent such as water, methanol, ethanol, THF, DMF and the like to givecompound [I-2-5]. When a salt of hydroxylamine such as hydrochloride andthe like is used, the reaction is carried out in the presence of a basesuch as sodium hydrogencarbonate, sodium hydroxide, triethylamine andthe like.

[1555] Production Method 2-3

[1556] Conversion of Sulfonic Acid Ester Moiety to Sulfonic Acid

[1557] wherein R^(c6) is C₁₋₆alkyl, and other symbols are as definedabove.

[1558] The compound [I-2-6] obtained in the same manner as in theabove-mentioned Production Method is reacted with iodide salt such assodium iodide, lithium iodide and the like, bromide salt such as sodiumbromide, trimethylammonium bromide and the like, amine such as pyridine,trimethylamine, triazole and the like, phosphine such astriphenylphosphine and the like in a solvent such as DMF, dimethylsulfoxide (DMSO), acetonitrile, methanol, ethanol, water and the likewith heating to give compound [I-2-7].

[1559] Production Method 3

[1560] This Production Method relates to convertion of thesubstituent(s) on phenyl group at the 2-position of benzimidazole. ThisProduction Method can be used even when phenyl is a different ring.

[1561] Production Method 3-1

[1562] Conversion of Hydroxyl Group to Ether

[1563] wherein R^(c7) is optionally substituted alkyl corresponding toR^(a11), G¹ is a single bond, *—(CH₂)_(n)—, *—(CH₂)_(n)—O—,*—(CH₂)_(n)—CO— or *—(CH₂)_(m)—CR^(a15)R^(a16))—(CH₂)_(n)—, wherein *show the side to be bonded to R^(c1), and other symbols are as definedabove.

[1564] When R^(c1) of compound [13] is halogen atom, compound [I-2-8]obtained in the same manner as in the above-mentioned Production Methodis reacted with compound [13] in a solvent such as DMF, DMSO,acetonitrile, ethanol, THF and the like in the presence of a base suchas sodium hydride, sodium hydroxide, potassium hydroxide, potassiumcarbonate, sodium ethoxide, potassium t-butoxide and the like at roomtemperature or with heating to give compound [II-2-1].

[1565] When R^(c1) of compound [13] is hydroxyl group, the hydroxylgroup of compound [13] is converted to halogen atom with thionylchloride, phosphorus tribromide, carbon tetrabromide-triphenylphosphineand the like and reacted with compound [I-2-8] by the aforementionedmethod to give compound [II-2-1]. In this case, compound [I-2-8] may besubjected to Mitsunobu reaction with compound [13] in a solvent such asDMF, acetonitrile, THF and the like using triphenylphosphine-diethylazodicarboxylate and the like to give compound [II-2-1].

[1566] The compound [I-2-9] can be obtained in the same manner fromcompound [I-2-8] and compound [14].

[1567] Production Method 3-2

[1568] Conversion of Nitro to Substituted Amino Group

[1569] wherein R^(c8) is C₁₆alkyl, G² is *—(CH₂)_(n)—or *—CHR^(a15), G³is —CO—, *—CO₂—, *—CONH or —SO₂—, and other symbols are as definedabove.

[1570] Step 1

[1571] The nitro compound [I-2-10] obtained in the same manner as in theabove-mentioned Production Method is reacted in the same manner as inStep 2 of Production Method 1-1 to give compound [I-2-11].

[1572] Step 2

[1573] The compound [I-2-11] is alkylated with compound [15] in the samemanner as in Production Method 3-1 to give compound [II-2-2].

[1574] Step 3

[1575] When G³ of compound [16] is —CO—, —CO₂— or —CONH—, compound[I-2-11] is acylated with compound [16] in the same manner as in Step 3of Production Method 1-1 to give compound [II-2-3].

[1576] When G³ of compound [16] is —SO₂—, sulfonylation is conductedusing sulfonyl halide instead of acid halide used in Step 3 ofProduction Method 1-1 to give compound [II-2-3].

[1577] The compound [I-2-11] is acylated with compound [17] in the samemanner as above to give compound [I-2-12].

[1578] This Production Method is applied in the same manner as above togive disubstituted compounds (tertiary amine) of compound [II-2-2],compound [II-2-3] and compound [I-2-12].

[1579] Production Method 3-3

[1580] Conversion of Carboxylic Acid Ester Moiety to Amide

[1581] wherein R^(c9) is C₁₋₆ alkyl, G⁴is #—(CH₂)_(n)—, #—(CH₂)—NH— or#—CHR^(a14)— wherein # shows the side that is bounded to amine and othersymbols are as defined above.

[1582] Step 1

[1583] The compound [I-2-13] obtained in the same manner as in theabove-mentioned Production Method is reacted in the same manner as inStep 1 of Production Method 2-1 to give compound [I-2-14].

[1584] Step 2

[1585] The compound [I-2-14] is reacted with compound [18] in the samemanner as in Step 2 of Production Method 2-1 to give compound [II-2-4].

[1586] The compound [I-2-15] is obtained from compound [I-2-14] andcompound [19] in the same manner as above.

[1587] Production Method 4

[1588] In this Production Method, additional substituent.(s) is(are)introduced into ring B on phenyl group that substitutes the 2-positionof benzimidazole. This Production Method is applicable even when phenylis a different ring.

[1589] Production Method 4-1

[1590] Direct Bonding of Ring Z″ to Ring B

[1591] wherein ring Z″—M is aryl metal compound, ring Z″ moiety isoptionally substituted C₆₋₁₄ aryl or optionally substituted heterocyclicgroup corresponding to substituent Z, and the metal moiety containsboron, zinc, tin, magnesium and the like, such as phenylboronic acid, w”is 0, 1 or 2, and other symbols are as defined above.

[1592] The compound [II-2-5] obtained in the same manner as in theabove-mentioned Production Method is reacted with aryl metal compound[20] in a solvent such as DMF, acetonitrile, 1,2-dimethoxyethane, THF,toluene, water and the like in the presence of a palladium catalyst suchas tetrakis(triphenylphosphine)-palladium,bis(triphenylphosphine)palladium(II) dichloride, palladiumacetate-triphenylphosphine and the like, a nickel catalyst such asnickel chloride, [1,3-bis(diphenylphosphino)-propane] nickel(II)chloride and the like, and a base such as potassium carbonate, potassiumhydrogencarbonate, sodium hydrogen-carbonate, potassium phosphate,triethylamine and the like at room temperature or with heating, to givecompound [II-2-6].

[1593] Production Method 4-2

[1594] Conversion of Hydroxyl Group to Ether

[1595] wherein R^(c10) is —R^(a20) or —(CH₂)_(p)—COR^(a21) correspondingto substituent Z, and other symbols are as defined above.

[1596] The compound [II-2-7] obtained in the same manner as in theabove-mentioned Production Method is reacted with compound [21] in thesame manner as in Production Method 3-1 to give compound [II-2-8].

[1597] Production Method 4-3

[1598] Synthesis in Advance of Ring B Part Such as Compound [13] inProduction Method 3-1

[1599] wherein R^(c11) is leaving group such as bromine atom, iodineatom, trifluoromethanesulfonyloxy and the like, R^(c12) is formyl,carboxyl or carboxylic acid ester such as methoxycarbonyl,ethoxycarbonyl, tert-butoxycarbonyl and the like, and other symbols areas defined above.

[1600] Step 1

[1601] Commercially available compound [22] or compound [22] obtained bya conventional method is reacted with aryl metal compound [20] in thesame manner as in Production Method 4-l to give compound [23].

[1602] Step 2

[1603] The compound [23] obtained in the same manner as in theabove-mentioned Production Method is reduced according to a conventionalmethod to give compound [24].

[1604] For example, compound [23] is reacted with in a solvent such asmethanol, ethanol, THF and the like in the presence of a reducing agentsuch as lithium aluminum hydride, sodium borohydride and the like undercooling to heating to give compound [24].

[1605] Step 3

[1606] The compound [24] obtained in the same manner as in theabove-mentioned Production Method is reacted in a solvent such as1,4-dioxane, diethyl ether, THF, dichloromethane, chloroform, tolueneand the like with a halogenating agent, such as phosphoruspentachloride, phosphorus tribromide, thionyl chloride and the like, inthe presence of a tertiary amine such as pyridine and the like to givecompound [25].

[1607] Step 4

[1608] The compound [24] or [25] obtained in the same manner as in theabove-mentioned Production Method is reacted with compound [I-2-8] inthe same manner as in Production Method 3-1 to give compound [II-2-9].

[1609] Production Method 4-4

[1610] wherein M′ is a metal such as magnesium, lithium, zinc and thelike, and other symbols are as defined above.

[1611] Step 1

[1612] Commercially available compound [41] or compound [41] obtained bya conventional method is converted to aryl metal reagent by aconventional method to give compound [42].

[1613] For example, when M′ is magnesium, magnesium is reacted withcompound [41] in a solvent such as THF, diethyl ether, benzene, tolueneand the like, preferably THF, from cooling to heating preferably at−100° C. to 100° C. to give compound [42].

[1614] Step 2

[1615] The compound [42] obtained in the same manner as in theabove-mentioned Production Method is reacted with compound [43] to givecompound [44].

[1616] The compound [42] is reacted in a solvent such as diethyl ether,benzene, toluene, THF and the like, preferably THF, from cooling to roomtemperature, preferably at −100° C. to 30° C. to give compound [44].

[1617] Step 3

[1618] The compound [44] obtained in the same manner as in theabove-mentioned Production Method is halogenated in the same manner asin Step 3 of Production Method 4-3 to give compound [45].

[1619] The compound [44] is reacted with thionyl chloride and pyridinepreferably in toluene solvent to give compound [45].

[1620] When compound [45] is symmetric, namely, when the ring B-(Z)wmoiety and the ring B′-(Z′)w′ moiety are the same, compound [42] isreacted with formate such as methyl formate, ethyl formate and the like,preferably ethyl formate, in a solvent such as diethyl ether, benzene,toluene, THF and the like, )preferably THF, from cooling to roomtemperature, preferably at −100° C. to 30° C., to give compound [45].

[1621] Production Method 4-5

[1622] Method Including Steps to Introduce a Protecting Group into aFunctional Group

[1623] wherein R^(c13) is carboxylic acid protecting group such astert-butyl and the like, R^(c14) is carboxylic acid protecting groupsuch as methyl and the like and other symbols are as defined above.

[1624] Step 1

[1625] Commercially available compound [26] or compound. [26] obtainedby a conventional method is protected by a conventional method to givecompound [27].

[1626] For example, when R^(c13) is tert-butyl, compound [26] isconverted to acid halide with thionyl chloride, oxalyl chloride and thelike in a solvent such as THF, chloroform, dichloromethane, toluene andthe like, and reacted with potassium tert-butoxide to give compound[27].

[1627] As used herein, R^(c13) may be a different protecting group aslong as it is not removed during the Step 2 or Step 3 but removed inStep 4 without affecting —CO₂R^(c14).

[1628] Step 2

[1629] The methyl group of compound [27] obtained in the same manner asin the above-mentioned Production Method is Converted to bromomethylwith N-bromosuccinimide and N,N′-azobisisobutyronitrile and reacted withcompound [I-2-1-16] in the same manner as in Production Method 3-1 togive compound [II-2-10].

[1630] Step 3

[1631] The compound [II-2-10] obtained in the same manner as in theabove-mentioned Production Method is reacted with aryl metal compound[20] in the same manner as in Production Method 4-1 to give compound[II-2-11].

[1632] Step 4

[1633] The R^(c13) of the compound [II-2-11] obtained in the same manneras in the above-mentioned Production Method is removed by a conventionalmethod to give compound [II-2-12].

[1634] The protecting group of carboxylic acid can be removed by aconventional deprotection method according to the protecting group. Inthis Step, the conditions free from reaction of R^(c14) are preferable.For example, when R^(c13) is tert-butyl, compound [II-2-11] is treatedwith trifluoroacetic acid in a solvent such as dichloromethane,chloroform and the like to give compound [II-2-12].

[1635] Step 5

[1636] The compound [II-2-12] obtained in the same manner as in theabove-mentioned Production Method is subjected to amide condensationwith compound [28] in the same manner as in Step 3 of Production Method1-1 to give compound [II-2-13].

[1637] Step 6

[1638] The compound [II-2-13] obtained in the same manner as in theabove-mentioned Production Method is deprotected in the same manner asin Step 1 of Production Method 2-1 to give compound [II-2-14].

[1639] As used herein, R^(c14) is preferably a protecting group thatdoes not react during the Step 1 through Step 5 but removed in thisStep.

[1640] For example, when R^(c14) is methyl, compound [II-2-13] isreacted in an alcohol solvent such as methanol, ethanol, n-propanol,isopropanol and the like or a mixed solvent of alcohol solvent and waterin the presence of a base such as potassium carbonate, sodium carbonate,lithium hydroxide, sodium hydroxide, potassium hydroxide and the likefrom cooling to heating for deprotection, followed by acidifying thereaction solution to give compound [II-2-14].

[1641] Production Method 4-6

[1642] wherein g is an integer of 1 to 5, and other sumbols are asdefined above.

[1643] Step 1

[1644] The compound [I-2-16] obtained by the above-mentioned ProductionMethod is reacted with toluene derivative [41] in the same manner as inStep 2 of Production Method 4-5 to give compound [II-2-17].

[1645] Step 2

[1646] The compound [II-2-17] obtained by the above-mentioned ProductionMethod is reacted with aryl metal compound [20] in the same manner as inProduction Method 4-1 to give compound [II-2-18].

[1647] Step 3

[1648] The compound [II-2-18] obtained by the above-mentioned ProductionMethod is reduced in the same manner as in ;Step 2 of Production Method1-1 to give compound [II-2-19].

[1649] Step 4

[1650] The compound [II-2-19] obtained by the above-mentioned ProductionMethod is amide condensed with compound [42] in the same manner as inStep 3 of Production Method 1-1 and subjected to cyclization in the samemanner as in Step 1 of Production Method 1-1 to give compound [II-2-20].

[1651] Step 5

[1652] The compound [II-2-20] obtained by the above-mentioned ProductionMethod is hydrolyzed in the same manner as in Step 1 of ProductionMethod 2-1 to give compound [II-2-21].

[1653] Production Method 5

[1654] Formation of Indole Ring

[1655] wherein R^(c15) is protecting group such as trimethylsilyl,tert-butyldimethylsilyl, tert-butyldiphenylsilyl and the like, and othersymbols are as defined above.

[1656] Step 1

[1657] The compound [29] obtained in the same manner as in theabove-mentioned Production Method or conventional method is reacted withcompound [30] in a solvent such as DMF, acetonitrile,1,2-dimethoxyethane, THF, toluene, water and the like using a palladiumcatalyst such as tetrakis(triphenylphosphine)palladium,bis(triphenylphosphine)palladium(II) dichloride, palladiumacetate-triphenylphosphine and the like, a copper catalyst such ascopper(I) iodide and the like or a mixture thereof, and in the presenceof a base such as potassium carbonate, potassium hydrogencarbonate,sodium hydrogencarbonate, potassium phosphate, triethylamine and thelike to give compound [31].

[1658] Step 2

[1659] The compound [31] obtained in the same manner as in theabove-mentioned Production Method is reacted in an alcohol solvent suchas methanol, ethanol and the like or a mixed solvent of an alcoholsolvent and a solvent such as DMF, acetonitrile, THF, chloroform,dichloromethane, ethyl acetate, methylene chloride, toluene and the likein the presence of a base such as potassium carbonate, sodium carbonate,lithium hydroxide, sodium hydroxide, potassium hydroxide, lithiumhydride, sodium hydride, potassium hydride and the like at roomtemperature or with heating for deprotection, and reacted with compound[32] obtained in the same manner as in Step 1 of Production Method 1-1in the same manner as in Step 1 of Production Method 5 to give compound[33].

[1660] Step 3

[1661] The compound [33] obtained in the same manner as in theabove-mentioned Production Method was subjected to cyclization in asolvent such as DMF, acetonitrile, THF, chloroform, dichloromethane,ethyl acetate, methylene chloride, toluene and the like in the presenceof a copper catalyst such as copper(I) iodide and the like or apalladium catalyst such as palladium(II) chloride and the like at roomtemperature or with heating to give compound [II-2-15].

[1662] Production Method 6

[1663] Formation of imidazo[1,2-a]pyridine Ring

[1664] wherein R^(c16) and R^(c17) are each independently alkyl, such asmethyl, ethyl and the like, and other symbols are as defined above.

[1665] Step 1

[1666] The compound [34] obtained by the above-mentioned ProductionMethod or a conventional method is subjected to amide condensation withcompound [35] in the same manner as in Step 3 of Production Method 1-1to give compound [36].

[1667] Step 2

[1668] The compound [36] obtained by the above-mentioned ProductionMethod is reacted with Grignard reagent [37] obtained by a conventionalmethod to give compound [38].

[1669] Alternatively, an acid halide of compound [34] may be usedinstead of compound [36].

[1670] Step 3

[1671] The compound [38] obtained by the above-mentioned ProductionMethod is subjected to halogenation by a conventional method to givecompound [39].

[1672] For example, when Hal is a bromine atom, compound [38] is reactedwith bromine under cooling or at room temperature in a solvent such asDMF, acetonitrile, THF, chloroform, dichloromethane, ethyl acetate,toluene and the like to give compound [39].

[1673] Alternatively, a halogenating agent such as hypohalite (e.g.,hypochlorite and the like), N-bromosuccinimide and the like may be usedinstead of bromine for halogenation.

[1674] Step 4

[1675] The compound [39] obtained by the above-mentioned ProductionMethod is subjected to cyclization with compound [40] obtained by aconventional or known method (JP-A-8-48651) in the presence of a basesuch as potassium carbonate, sodium carbonate, lithium hydroxide, sodiumhydroxide, potassium hydroxide, lithium hydride, sodium hydride,potassium hydride and the like in a solvent or without a solvent at roomtemperature or with heating to give compound [II-2-16].

[1676] In the compounds of the formulas [I] and [II], a desiredheterocyclic group can be formed according to a method similar to themethods disclosed in known publications. Examples of such heterocyclicgroup and reference publications are recited in the following.

[1677] 5-oxo-Δ²-1,2,4-oxadiazolin-3-yl (or2,5-dihydro-5-oxo—4H-1,2,4-oxadiazol-3-yl),5-oxo-Δ²-1,2,4-thiadiazolin-3-yl (or2,5-dihydro-5-oxo-4H-1,2,4-thiadiazol-3-yl),2-oxo-Δ³-1,2,3,5-oxathiadiazolin-4-yl (or2-oxo-Δ³-1,2,4-oxathiadiazol-4-yl): Journal of Medicinal Chemistry,39(26), 5228-35, 1996,

[1678] 5-oxo-Δ²-1,2,4-triazolin-3-yl: J Org Chem, 61(24), 839)7-8401,1996,

[1679] 1-oxo-Δ³-1,2,3,5-thiatriazolin-4-yl: Liebigs Ann Chem, 1376,1980,

[1680] 3-oxo-Δ⁴-1,2,4-oxadiazolin-5-yl: EP145095,

[1681] 5-oxo-Δ²-1,3,4-oxadiazolin-2-yl: J Org Chem, 20, 412, 1955,

[1682] 5-oxo-Δ³-1,2,4-dioxazolin-3-yl: J Prakt Chem, 314, 145, 1972,

[1683] 3-oxo-Δ⁴-1,2,4-thiadiazolin-5-yl: JP-A-61-275271,

[1684] 5-oxo-Δ³-1,2,4-dithiazolin-3-yl: J Org Chem, 61(19), 6639-6645,1996,

[1685] 2-oxo-Δ⁴-1,3,4-dioxazolin-5-yl: J Org Chem, 39, 2472, 1974,

[1686] 2-oxo-Δ⁴-1,3,4-oxathiazolin-5-yl: J Med Chem, 35(20), 3691-98,1992,

[1687] 5-oxo-Δ²-1,3,4-thiadiazolin-2-yl: J Prakt Chem, 332(1), 55, 1990,

[1688] 5-oxo-Δ²-1,4,2-oxathiazolin-3-yl: J Org Chem, 31, 2417, 1966,

[1689] 2-oxo-Δ⁴-1,3,4-dithiazolin-5-yl: Tetrahedron Lett, 23, 5453,1982,

[1690] 2-oxo-Δ⁴-1,3,2,4-dioxathiazolin-5-yl: Tetrahedron Lett:, 319,1968,

[1691] 3,5-dioxoisooxazolidin-4-yl: Helv Chim Acta, 1973, 48, 1965,

[1692] 2,5-dioxoimidazolidin-4-yl: Heterocycles, 43(1), 49-5(1), 1996,

[1693] 5-oxo-2-thioxoimidazolidin-4-yl: Heterocycles, 5, 391, 1983,

[1694] 2,4-dioxooxazolidin-5-yl: J Am Chem Soc, 73, 4752, 1951,

[1695] 4-oxo-2-thioxooxazolidin-5-yl: Chem Ber, 91, 300, 19513,

[1696] 2,4-dioxothiazolidin-5-yl: JP-A-57-123175,

[1697] 4-oxo-2-thioxothiazolidin-5-yl: Chem Pharm Bull, 30, :3563, 1982,

[1698] The Production Methods shown in the above-mentioned ProductionMethods 2 to 4 can be used for the synthesis of compounds other thanbenzimidazole of the formulas [I] and [II], such as compounds [II-2-15]and [II-2-16].

[1699] The compounds of the formulas [I], [II] and [III],4-(4-fluorophenyl)-5-hydroxymethyl-2-methylthiazole and4-(4-fluorophenyl)-5-chloromethyl-2-methylthiazole and productionmethods thereof of the present invention are explained in detail in thefollowing by way of Examples. It is needless to say that the presentinvention is not limited by these Examples.

EXAMPLE 1

[1700] Production of Ethyl2-[4-(3-bromophenoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylate

[1701] Step 1: Production of Ethyl 4-chloro-3-nitrobenzoate

[1702] 4-Chloro-3-nitrobenzoic acid (300 g) was dissolved in ethylalcohol (1500 ml) and concentrated sulfuric acid (100 ml) was added withice-cooling. The mixture was refluxed under: heating for 7 hr. Thereaction mixture was poured into ice-cold water and the precipitatedcrystals were collected by filtration to give the title compound (332 g,yield 97%).

[1703]¹H-NMR (300 MHz, CDCl₃): 8.50 (1H, d, J=2.1 Hz), 8.16 (1H, dd,J=8.4, 2.1 Hz), 7.63 (1H, d, J=8.4 Hz), 4.43 (2H, q, J=7.5 Hz), 1.42(3H, t, J=7.5 Hz).

[1704] Step 2: Production of Ethyl 4-cyclohexylamino-3-nitrobenzoate

[1705] Ethyl 4-chloro-3-nitrobenzoate (330 g) obtained in the previousstep was dissolved in acetonitrile (1500 ml), and cyclohexylamine (220g) and triethylamine (195 g) were added. The mixture was refluxed underheating overnight. The reaction mixture was poured into ice-cold waterand the precipitated crystals were collected by filtration to give thetitle compound (400 g, yield 94%).

[1706]¹H-NMR (300 MHz, CDCl₃): 8.87 (1H, d, J=2.1 Hz), 8.35-8.46 (1H,m), 8.02 (1H, dd, J=9.1, 2.1 Hz), 6.87 (1H, d, J=9.1 Hz), 4.35 (2H, q,J=7.1 Hz), 3.65-3.50 (1H, m), 2.14-1.29 (10H, m), 1.38 (3H, t, J=7.1Hz).

[1707] Step 3: Production of Ethyl 3-amino-4-cyclohexylaminobenzoate

[1708] Ethyl 4-cyclohexylamino-3-nitrobenzoate (400 g) obtained in theprevious step was dissolved in ethyl acetate (1500 ml) and ethyl alcohol(500 ml), and 7.5% palladium carbon (50% wet, 40 g) was added. Themixture was hydrogenated for 7 hr at atmospheric pressure. The catalystwas filtered off and the filtrate was concentrated under reducedpressure. Diisopropyl ether was added to the residue and theprecipitated crystals were collected by filtration to give the titlecompound (289 g, yield 80%).

[1709]¹H-NMR (300 MHz, CDCl₃): 7.57 (1H, dd, J=8.4, 1.9 Hz), 7.41 (1H,d, J=1.9 Hz), 6.59 (1H, d, J=8.4 Hz), 4.30 (2H, q, J=7.1 Hz), 3.40-3.30(1H, m), 2.18-2.02 (2H, m), 1.88-1.15 (8H, m), 1.35 (3H, t, J=7.1 Hz).

[1710] Step 4: Production of Ethyl3-[4-(3-bromophenoxy)benzoyl]amino-4-cyclohexylaminobenzoate

[1711] 4-(3-Bromophenoxy)benzoic acid (74 g) was dissolved in chloroform(500 ml), and oxalyl chloride (33 ml) and dimethylformamide (catalyticamount) were added. The mixture was stirred for 4 hr at roomtemperature. The reaction mixture was concentrated under reducedpressure and dissolved in dichloromethane (150 ml). The resultingsolution was added dropwise to a solution of ethyl3-amino-4-cyclohexylaminobenzoate (66 g) obtained in the previous stepin dichloromethane (500 ml) and triethylamine (71 ml), and the mixturewas stirred for 1 hr at room temperature. The reaction mixture waspoured into water and extracted with dichloromethane. The organic layerwas washed with saturated brine, dried over anhydrous magnesium sulfate,and concentrated under reduced pressure. Diethyl ether was added to theresidue for crystallization and the crystals were collected byfiltration to give the title compound (129 g, yield 95%).

[1712]¹H-NMR (300 MHz, CDCl₃): 8.00-7.78 (4H, m), 7.66 (1H, brs),7.37-7.18 (3H, m), 7.13-6.59 (3H, m), 6.72 (1H, d, J=8.7 Hz), 4.50 (1H,brs), 4.29 (2H, q, J=7.2 Hz), 3.36 (1H, m), 2.12-1.96 (2H, m), 1,83-1.56 (3H, m), 1.47-1.12 (5H, m), 1.37 (3H, t, J=7.2 Hz).

[1713] Step 5: Production of Ethyl2-[4-(3-bromophenoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylate

[1714] Ethyl3-[4-(3-bromophenoxy)benzoyl]amino-4-cyclohexylaminobenzoate (129 g)obtained in the previous step was suspended in acetic acid (600 ml) andthe resulting suspension was refluxed under heating for 3 hr. Thereaction mixture was concentrated under reduced pressure. Water wasadded to the residue and the precipitated crystals were collected byfiltration to give the title compound (124 g, yield 99v).

[1715]¹H-NMR (300 MHz, CDCl₃): 8.51 (1H, d, J=1.5 Hz), 8.00 (1H, dd,J=8.4, 1.5 Hz), 7.67 (1H, d, J=8.4 Hz), 7.63 (2H, d, J=8.7 Hz),7.35-7.21 (3H, m), 7.17 (2H, d, J=8.7 Hz), 7.14 (1H, m), 4.42 (2H, q,J=7.2 Hz), 4.38 (1H, m), 2.43-2.22 (2H, m), 2.07-1.87 (4H, m), 1.80 (1H,m), 1.42 (3H, t, J=7.2 Hz), 1.40-1.27 (3H, m).

EXAMPLE 2

[1716] Production of2-[4-(3-bromophenoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylic Acid

[1717] Ethyl2-[4-(3-bromophenoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylate(1.0 g) obtained in Example 1 was dissolved in tetrahydrofuran (10 ml)and ethyl alcohol (10 ml), and 4N sodium hydroxide (10 ml) was added.The mixture was refluxed under heating for 1 hr. The reaction mixturewas concentrated under reduced pressure and water was added to theresidue. The mixture was acidified with 6N hydrochloric acid and theprecipitated crystals were collected by filtration to give the titlecompound (0.9 g, yield 96%). melting point: 255-256° C.

[1718] FAB-Ms: 491 (MH+).

[1719]¹H-NMR (300 MHz, DMSO-d₆): (12.75 (1H, brs), 8.24 (1H, s), 7.96(1H, d, J=8.7 Hz), 7.86 (1H, d, J=8.7 Hz), 7.71 (2H, d, J=8.6 Hz),7.47-7.34 (3H, m), 7.24 (2H, d, J=8.6 Hz), 7.20 (1H, m), 4.31 (1H, m),2.38-2.18 (2H, m), 2.02-1.79 (4H, m), 1.65 (1H, m), 1.44-1.20 (3H, m).

EXAMPLE 3

[1720] Production of Ethyl1-cyclohexyl-2-(4-hydroxyphenyl)benzimidazole-5-carboxylate

[1721] Ethyl 3-amino-4-cyclohexylaminobenzoate (130 g) obtained inExample 1, Step 3, and methyl 4-hydroxybenzimidate hydrochloride (139 g)were added to methyl alcohol (1500 ml), and the mixture was refluxedunder heating for 4 hr. The reaction mixture was allowed to cool and theprecipitated crystals were collected by filtration to give the titlecompound (131 g, yield 72%).

[1722]¹H-NMR (300 MHz, CDCl₃): 10.02 (1H, brs), 8.21 (1H, d, J=1.4 Hz),7.93 (1H, d, J=8.6 Hz), 7.83 (1H, dd, J=8.6, 1.4 Hz), 7.48 (2H, d, J=8.6Hz), 6.95 (2H, d, J=8.6 Hz), 4.39-4.25 (1H, m), 4.33 (1H, q, J=7.0 Hz),2.35-2.18 (2H, m), 1.98-1.79 (4H, m), 1.70-1.60 (1H, m), 1.46-1.19 (3H,m), 1.35 (3H, t, J=7.0 Hz).

EXAMPLE 4

[1723] Production of Ethyl2-[4-(2-bromo-5-chlorobenzyloxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylate

[1724] 2-Bromo-5-chlorobenzyl bromide prepared from2-bromo-5-chlorotoluene (50 g), N-bromosuccinimide andN,N′-azobisisobutyronitrile, and ethyl1-cyclohexyl-2-(4-hydroxyphenyl)benzimidazole-5-carboxylate (50 g)obtained in Example 3 were suspended in dimethylformamide (300 ml).Potassium carbonate (38 g) was added and the mixture was stirred for 1hr at 80° C. with heating. The reaction mixture was allowed to cool andthen added to a mixed solvent of water-ethyl acetate. The precipitatedcrystals were collected by filtration to give the title compound (50 g,yield 64%).

[1725]¹H-NMR (300 MHz, CDCl₃): 8.50 (1H, d, J=1.4 Hz), 7.97 (1H, dd,J=8.6, 1.4 Hz), 7.70-7.57 (5H, m), 7.20 (1H, dd, J=8.4, 2.5 Hz), 7.14(2H, d, J=8.7 Hz), 5.17 (2H, s), 4.46-4.30 (1H, m), 4.41 (2H, q, J=7.1Hz), 2.40-2.20 (2H, m), 2.02-1.21 (8H, m), 1.42 (3H, t, J=7.1 Hz).

EXAMPLE 5

[1726] Production of Ethyl2-{4-[2-(4-chlorophenyl)-5-chlorobenzyloxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylate

[1727] Ethyl2-[4-(2-bromo-5-chlorobenzyloxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylate(49 g) obtained in Example 4, 4-chlorophenylboronic acid (18 g) andtetrakis-(triphenylphosphine)palladium (10 g) were suspended in1,2-dimethoxyethane (600 ml). Saturated aqueous sodium hydrogencarbonatesolution (300 ml) was added and the mixture was refluxed under heatingfor 2 hr. Chloroform was added to the reaction mixture. The organiclayer was washed successively with saturated aqueous sodiumhydrogencarbonate solution, waiter and saturated brine, dried overanhydrous magnesium sulfate, and concentrated under reduced pressure.The residue was purified by silica gel flash chromatography (developingsolvent, chloroform:methyl acetate=97:3). Ethyl acetate and diisopropylether were added to the resulting oil for crystallization and theresulting crystals were collected by filtration to give the titlecompound (44 g, yield 85%).

[1728]¹H-NMR (300 MHz, CDCl₃): 8.49 (1H, d, J=1.4 Hz), 7.97 (1H, dd,J=8.6, 1.6 Hz), 7.70-7.60 (2H, m), 7.55 (2H, d, J=8.7 Hz), 4.95 (2H, s),4.48-4.28 (1H, m), 4.40 (2H, m), 2.02-1.20 (8H, m), 1.41 (3H, t, J=7.1Hz).

EXAMPLE 6

[1729] Production of2-{4-[2-(4-chlorophenyl)-5-chlorobenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicAcid

[1730] Ethyl2-{4-[2-(4-chlorophenyl)-5-chlorobenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylate(43 g) obtained in Example 5 was treated in the same manner as inExample 2 to give the title compound (33 g, yield 76%).

[1731] melting point: 243-244° C.

[1732] FAB-Ms: 571 (MH+).

[1733]¹H-NMR (300 MHz, DMSO-d₆): 8.32 (1H, s), 8.28 (1H, d, J=8.9 Hz)8.05 (1H, d, J=8.8 Hz), 7.76-7.72 (3H, m), 7.58-7.46 (5H, m), 7.40 (1H,d, J=8.3 Hz), 7.24 (2H, d, J=8.9 Hz), 5.11 (2H, s), 4.36 (1H, m),2.40-2.15 (2H, m), 2.15-1.95 (2H, m), 1.95-1.75 (2H, m), 1.75-1.55 (1H,m), 1.55-1.15 (3H, m).

EXAMPLE 7

[1734] Production of Ethyl2-[4-(2-bromo-5-methoxybenzyloxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylate

[1735] Ethyl 1-cyclohexyl-2-(4-hydroxyphenyl)benzimidazole-5-carboxylateobtained in Example 3 and 2-bromo-5-methoxybenzyl bromide were treatedin the same manner as in Example 4 to give the title compound (59 g).

EXAMPLE 8

[1736] Production of Ethyl2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylate

[1737] Ethyl2-[4-(2-bromo-5-methoxybenzyloxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylateobtained in Example 7 was treated in the same manner as in Example 5 togive the title compound (48 g, yield 77%).

[1738]¹H-NMR (300 MHz, CDCl₃): 8.49 (1H, d, J=1.4 Hz), 7.97 (1H, dd,J=8.6, 1.4 Hz), 7.64 (1H, d, J=8.6 Hz), 7.54 (2H, d, J=8.7 Hz), 7.37(2H, d, J=8.6 Hz), 7.31 (2H, d, J=8.6 Hz), 7.25 (1H, d, J=8.4 Hz), 7.19(1H, d, J=2.7 Hz), 7.00 (2H, d, J=8.7 Hz), 6.97 (1H, dd, J=8.4, 2.7 Hz),4.98 (2H, s), 4.41 (2H, q, J=7.1 Hz), 4.42-4.29 (1H, m), 3.88 (3H, s),2.40-2.20 (2H, m), 2.01-1.88 (4H, m), 1.83-1.73 (1H, m), 1.42 (3H, t,J=7.1 Hz), 1.41-1.25 (3H, m).

EXAMPLE 9

[1739] Production of2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicAcid

[1740] Ethyl2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylate(52 g) obtained in Example 8 was treated in the same manner as inExample 2 to give the title compound (44 g, yield 89%).

[1741] melting point: 248-249° C.

[1742] FAB-Ms: 568 (MH+).

[1743]¹H-NMR (300 MHz, DMSO-d₆): 8.20 (1H, s), 7.88 (1H, d, J=8.7 Hz),7.85 (1H, d, J=8.7 Hz), 7.57 (d, 2H, J=8.6 Hz), 7.46 (2H, d, J=8.6 Hz),7.44 (2H, d, J=8.6 Hz), 7.29 (1H, d, J=8.5 Hz), 7.24 (1H, d, J=2.6 Hz),7.11 (2H, d, J=8.6 Hz), 7.06 (1H, dd, J=8.5, 2.6 Hz), 5.04 (2H, s), 4.26(1H, m), 3.83 (3H, s), 2.38-2.29 (2H, m).

EXAMPLE 10

[1744] Production of Ethyl1-cyclohexyl-2-{4-[(E)-2-phenylvinyl]phenyl}-benzimidazole-5-carboxylate

[1745] Ethyl 3-amino-4-cyclohexylaminobenzoate (500 mg) obtained inExample 1, Step 3, was dissolved in methyl alcohol (6 ml) andtrans-4-stilbenecarbaldehyde (397 mg) was added under ice-cooling. Themixture was stirred overnight at room temperature. The reaction mixturewas ice-cooled and benzofuroxan (259 mg) dissolved in acetonitrile (2ml) was added. The mixture was stirred for 7 hr at 50° C. The reactionmixture was ice-cooled. After 1N sodium hydroxide was added, ethylacetate was added and the mixture was extracted. The organic layer waswashed with water and saturated brine, dried over anhydrous magnesiumsulfate, and concentrated under reduced pressure. The residue waspurified by silica gel flash chromatography (developing solvent,n-hexane:ethyl acetate=4:1) to give the title compound (540 mg, yield63%).

[1746]¹H-NMR (300 MHz, DMSO-d₆): 8.28 (1H, d, J=1.4 Hz), 8.01 (1H, d,J=8.7 Hz), 7.90-7.80 (3H, m), 7.75-7.65 (4H, m), 7.50-7.25 (5H, m), 4.35(2H, q, J=7.0 Hz), 4.31 (1H, m), 2.40-2.20 (2H, m), 2.00-1.80 (4H, m),1.63 (1H, m), 1.40-1.20 (3H, m), 1.36 (3H, t, J=7.0 Hz).

EXAMPLE 11

[1747] Production of1-cyclohexyl-2-{4-[(E)-2-phenylvinyl]phenyl}-benzimidazole-5-carboxylicAcid

[1748] Ethyl1-cyclohexyl-2-{4-[(E)-2-phenylvinyl]phenyl}-benzimidazole-5-carboxylate(127 mg) obtained in Example 10 was treated in the same manner as inExample 2 to give the title compound (116 mg, yield 97%).

[1749] melting point: not lower than 300° C.

[1750] FAB-Ms: 423 (MH+).

[1751]¹H-NMR (300 MHz, DMSO-d₆): 8.25 (1H, s), 7.96-7.29 (13H, m)r, 4.33(1H, brt), 2.41-2.23 (2H, m), 2.03-1.78 (4H, m), 1.71-1.59 (1H, m),1.49-1.20 (3H, m).

EXAMPLE 12

[1752] Production of2-(4-benzyloxyphenyl)-1-cyclopentylbenzimidazole-5-carboxylic Acid

[1753] In the same manner as in Examples 1 and 2, the title compound(700 mg) was obtained.

[1754] FAB-Ms: 413 (MH+).

[1755]¹H-NMR (300 MHz, CDCl₃): 8.60 (1H, s), 8.04 (1H, d, J=9.0 Hz),7.63 (2H, d, J=8.4 Hz), 7.51-7.32 (6H, m), 7.14 (2H, d, J=9.0 Hz), 5.16(2H, s), 5.03-4.89 (1H, m), 2.41-1.63 (8H, m).

EXAMPLE 13

[1756] Production of2-(4-benzyloxyphenyl)-1-cyclopentylbenzimidazole-5-carboxamide

[1757] 2-(4-Benzyloxyphenyl)-1-cyclopentylbenzimidazole-5-carboxylicacid (700 mg) obtained in Example 12 was dissolved in dimethylformamide(10 ml), and ammonium chloride (108 mg),1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (390 mg),1-hydroxybenzotriazole (275 mg) and triethylamine (0.3 ml) were added.The mixture was stirred overnight at room temperature. Water was addedto the reaction mixture and the mixture was extracted with ethylacetate. The organic layer was washed successively with saturatedaqueous sodium hydrogencarbonate, water and saturated brine, dried overanhydrous magnesium sulfate, and concentrated under reduced pressure.Ethyl acetate and diisopropyl ether were added to the residue forcrystallization and the crystals were collected by filtration to givethe title compound (571 mg, yield 81%).

[1758] melting point: 232-233° C.

[1759] FAB-Ms: 412 (MH+).

[1760]¹H-NMR (300 MHz, CDCl₃): 8.23 (1H, d, =1.5 Hz), 7.86 (1H, dd,J=8.5, 1.5 Hz), 7.65-7.30 (8H, m), 7.13 (2H, d, J=8.8 Hz), 5.16 (2H, s),4.93 (1H, quint, J=8.8 Hz), 2.40-1.60 (8H, m).

EXAMPLE 14

[1761] Production of2-(4-benzyloxyphenyl)-5-cyano-1-cyclopentylbenzimidazole

[1762] In the same manner as in Example 1, the title compound (400 mg)was obtained.

[1763] FAB-Ms: 394 (MH+).

[1764]¹H-NMR (300 MHz, CDCl₃): 8.11 (1H, s), 7.68-7.30 (9H, m), 7.13(2H, s), 5.16 (2H, s), 4.94 (1H, quint, J=8.9 Hz), 2.35-1.60 (8H, m).

EXAMPLE 15

[1765] Production of2-(4-benzyloxyphenyl)-1-cyclopentylbenzimidazole-5-carboxamide Oxime

[1766] 2-(4-Benzyloxyphenyl)-5-cyano-1-cyclopentylbenzimidazole (400 mg)obtained in Example 14 was suspended in ethyl alcohol (3 ml) and water(1.5 ml), and hydroxylamine hydrochloride (141 mg) and sodiumhydrogencarbonate (170 mg) were added. The mixture was refluxed underheating overnight. The reaction mixtures was allowed to cool and theprecipitated crystals were collected by filtration to give the titlecompound (312 mg, yield 71%).

[1767] melting point: 225-226° C.

[1768] FAB-Ms: 456 (MH+).

[1769]¹H-NMR (300 MHz, DMSO-d₆): 8.20 (1H, s), 7.50-7.31 (9H, m), 7.12(2H, d, J=8.7 Hz), 5.15 (2H, s), 4.94 (1H, quint, J=8.7 Hz), 3.61 (3H,s), 3.40 (3H, s), 2.41-1.42 (8H, m).

EXAMPLE 16

[1770] Production of ethyl1-cyclohexyl-2-{4-[{4-(4-fluorophenyl)-2-methyl-5-thiazolyl}ethoxy]phenyl}benzimidazole-5-carboxylate

[1771] Step 1: Production of4-(4-fluorophenyl)-5-hydroxymethyl-2-methylthiazole

[1772] Ethyl 4-(4-fluorophenyl)-2-methyl-5-thiazolecarboxylate (59 g)prepared by a known method (Chem. Pharm. Bull., 43 (6), 947, 1995) wasdissolved in tetrahydrofuran (700 ml). Lithium aluminum hydride (13 g)was added under ice-cooling and the mixture was stirred for 30 min.Water (13 ml), 15% sodium hydroxide (13 ml) and water (39 ml) were addedsuccessively to the reaction mixture, and the precipitated insolublematerials were filtered off. The filtrate was concentrated under reducedpressure to give the title compound (37 g, yield 71%).

[1773]¹H-NMR (300 MHz, CDCl₃): 7.60 (2H, dd, J=8.7, 6.6 Hz), 7.11 (2H,t, J=8.7 Hz), 4.80 (2H, s), 2.70 (3H, s).

[1774] Step 2: Production of5-chloromethyl-4-(4-fluorophenyl)-2-methylthiazole

[1775] 4-(4-Fluorophenyl)-5-hydroxymethyl-2-methylthiazole (37 g)obtained in the previous step was dissolved in chloroform (500 ml), andthionyl chloride (24 ml) and pyridine (2 ml)-;were added. The mixturewas stirred for 3 hr at room temperature. The reaction mixture waspoured into ice-cold water. The mixture was extracted with chloroform,and washed with water and saturated brine. The organic layer was driedover sodium sulfate, and concentrated under reduced pressure to give thetitle compound (29 g, yield 76%).

[1776]¹H-NMR (300 MHz, CDCl₃): 7.67 (2H, dd, J=8.8, 5.4 Hz), 7.16 (2H,t, J=8.7 Hz), 4.79 (2H, s), 2.73 (3H, s).

[1777] Step 3: Production of Ethyl1-cyclohexyl-2-{4-{[4-(4-fluorophenyl)-2-methyl-5-thiazolyl}methoxy]phenyl}benzimidazole-5-carboxylate

[1778] 5-Chloromethyl-4-(4-fluorophenyl)-2-methylthiazole (28 g)obtained in the previous step and ethyl1-cyclohexyl-2-(4-hydroxyphenyl)benzimidazole-5-carboxylate (36 g)obtained in Example 3 were treated in the same manner as in Example 4 togive the title compound (61 g, yield 100%).

[1779] APCI-Ms: 570 (MH+).

[1780]¹H-NMR (300 MHz, DMSO-d₆): 8.25 (1H, d, J=1.5 Hz), 7.97 (1H, d,J=8.7 Hz), 7.86 (1H, dd, J=8.6, 1.6 Hz), 7.74 (2H, dd, J=8.8, 5.5 Hz),7.62 (2H, d, J=8.7 Hz), 7.33 (2H, t, J=8.9 Hz), 7.22 (2H, t, J=8.9 Hz),5.41 (2H, s), 4.34 (2H, q, J=7.1 Hz), 4.31 (1H, m), 2.71 (3A, s),2.40-2.15 (2H, m), 2.05-1.75 (4H, m), 1.55-1.15 (3H, m), 1.36 (3H, t,J=7.1 Hz).

EXAMPLE 17

[1781] Production of1-cyclohexyl-2-{4-[{4-(4-fluorophenyl)-2-methyl-5-thiazolyl}methoxy]phenyl}benzimidazole-5-carboxylicAcid

[1782] Ethyl1-cyclohexyl-2-{4-[{4-(4-fluorophenyl)-2-methyl-5-thiazolyl}methoxy]phenyl}benzimidazole-5-carboxylate(60 g) obtained in Example 16 was treated in the same manner as inExample 2 to give the title compound (39 g, yield 69%).

[1783] melting point: 196-198° C.

[1784] FAB-Ms: 542 (MH+).

[1785]¹H-NMR (300 MHz, DMSO-d₆): 13.1 (1H, brs), 8.34 (1H, s), 8.29 (1H,d, J=8.8 Hz), 8.06 (1H, d, J=8.7 Hz), 7.80-7.72 (4H, m), 7.36-7.31 (4H,m), 5.46 (2H, s), 4.38 (1H, m), 2.72 (3H, s), 2.45-2.15 (2H, m),2.15-1.95 (2H, m), 1.95-1.75 (2H, m), 1.75-1.55 (1H, m), 1.55-1.20 (3H,m).

EXAMPLE 18

[1786] Production of Ethyl1-cyclohexyl-2-(2-fluoro-4-hydroxyphenyl)-benzimidazole-5-carboxylate

[1787] In the same manner as in Example 3, the title compound (50 g) wasobtained.

EXAMPLE 19

[1788] Production of Ethyl2-{4-[bis(3-fluorophenyl)methoxyl]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylate

[1789] Step 1: Production of 3,3′-difluorobenzhydrol

[1790] To a stirred solution of magnesium strip (35.4 g) in THF (200ml), iodine strip was added and the mixture was heated with stirringunder nitrogen stream until most of color of iodine was disappeared. Asolution of 3-fluoro-bromobenzene (250.0 g) in THF (1000 ml) was addeddropwise over 2.5 hr while the temperature of the solution wasmaintained at 60° C. After the completion of the addition of thesolution, the resulting mixture was refluxed for 1 hr with heating. Theresulting Grignard solution was ice-cooled and a solution of ethylformate (63.2 g) in THF (200 ml) was added dropwise over 1 hr. After astirring of the reaction solution for an additional 30 min, saturatedaqueous ammonium chloride solution (700 ml) was added dropwise withice-cooling and water (300 ml) was added. The mixture was stirred for 10min. The organic layer and water layer were separated. Water layer wasextracted with ethyl acetate, and the combined organic layer was washedwith 2N hydrochloric acid, saturated aqueous sodium hydrogencarbonateand saturated brine. The organic layer was dried over anhydrousmagnesium sulfate, filtered, and the solvent was evaporated off underreduced pressure to give the title compound (156.2 g, yield 99%).

[1791]¹H-NMR (300 MHz, CDCl₃): 7.31 (2H, td, J=7.9, 5.8 Hz), 7.15-7.80(4H, m), 6.97-6.94 (2H, m), 5.82 (1H, d, J=3.3 Hz), 2.30 (1H, d, J=3.3Hz).

[1792] Step 2: Production of 3,3′-difluorobenzhydryl Chloride

[1793] To a solution of 3,3′-difluorobenzhydrol (150.0 g) obtained inthe previous step in toluene (400 ml), pyridine (533 mg) was added atroom temperature. To the solution, thionyl chloride (89.1 g) was addeddropwise over 1 hr at room temperature and the resulting solution wasstirred for an additional 2 hr. The solution was heated so that thetemperature of the solution was at 40° C., and then stirred for anadditional 1.5 hr. Thionyl chloride (8.1 g) was added again and themixture was stirred for 30 min. To the reaction mixture, water wasadded. The organic layer was separated, and washed with water, saturatedaqueous sodium hydrogencarbonate and saturated brine. The organic layerwas dried over anhydrous magnesium sulfate, filtered, the solvent wasevaporated off under reduced pressure to give the title compound (158.2g, yield 97%).

[1794]¹H-NMR (300 MHz, CDCl₃): 7.32 (2H, td, J=8.0, 5.9 Hz), 7.18-7.10(4H, m), 7.01 (2H, tdd, J=8.2, 2.5, 1.2 Hz), 6.05 (1H, s).

[1795] Step 3: Production of Ethyl2-{4-[bis(3-fluorophenyl)methoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylate

[1796] Ethyl1-cyclohexyl-2-(2-fluoro-4-hydroxyphenyl)-benzimidazole-5-carboxylate(50 g) obtained in Example 18 and 3,3′-difluorobenzhydryl chloride (34g) obtained in the previous step were treated in the same manner as inExample 4 to give the title compound (76 g, yield 99%).

[1797] FAB-Ms: 585 (MH+).

[1798]¹H-NMR (300 MHz, DMSO-d₆): 8.24 (1H, d, J=1.4 Hz), 7.98 (1, d,J=8.7 Hz), 7.88 (1H, d, J=8.7 Hz), 7.56 (1H, t, J=8.6 Hz), 7.50-7.40(6H, m), 6.82 (1H, s), 4.34 (2H, q, J=7.1 Hz), 3.95 (1H, m), 2.20-2.10(2H, m), 1.90-1.80 (4H, m), 1.6 (1H, m), 1.35 (3w, t, J=7.2 Hz),1.30-1.20 (3H, m).

EXAMPLE 20

[1799] Production of2-{4-(bis[3-fluorophenyl]methoxy)-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicAcid

[1800] Ethyl2-{4-[bis(3-fluorophenyl)methoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylate(75 g) obtained in Example 19 was treated in the same manner as inExample 2 to give the title compound (48 g, yield 62%). melting point:242-243° C.

[1801] FAB-Ms: 557 (MH+).

[1802]¹H-NMR (300 MHz, DMSO-d₆): 8.29 (1H, s), 8.16 (1H, d, J=8.88 Hz)7.99 (1H, d, J=8.7 Hz), 7.66 (1H, t, J=8.7 Hz), 7.51-7.40 (6H, m), 7.30(1H, d, J=12.1 Hz), 7.20-7.14 (3H, m), 6.88 (1H, s), 4.07 (1H, m),2.40-2.10 (2H, m), 2.00-1.75 (4H, m), 1.70-1.55 (1H, m), 1.50-1.15 (3H,m).

EXAMPLE 21

[1803] Production of Ethyl1-cyclopentyl-2-(4-nitrophenyl)benzimidazole-5-carboxylate

[1804] In the same manner as in Example 1, the title compound (12 g) wasobtained.

EXAMPLE 22

[1805] Production of Ethyl2-(4-aminophenyl)-1-cyclopentylbenzimidazole-5-carboxylate

[1806] Ethyl 1-cyclopentyl-2-(4-nitrophenyl)benzimidazole-5-carboxylate(12 g) obtained in Example 21 was dissolved in tetrahydrofuran (200 ml)and ethyl alcohol (50 ml), 7.5% palladium carbon (50% wet, 1 g) wasadded. The mixtures was hydrogenated for 1 hr at atmospheric pressure.The catalyst was filtered off and the filtrate was concentrated underreduced pressure. Tetrahydrofuran was added to the residue to allowcrystallization and the crystals were collected by filtration to givethe title compound (11 g, yield 98%).

[1807]¹H-NMR (300 MHz, CDCl₃): 8.49 (1H, d, J=1.3 Hz), 7.95 (1H, dd,J=8.5, 1.3 Hz), 7.50-7.40 (3H, m), 6.79 (2H, d, J=4.6 Hz), 4.97 (1H,quint, J=8.9 Hz), 4.40 (2H, q, J=7.1 Hz), 3.74 (2H, brs), 2.40-1.50 (8H,m), 1.41 (3H, t, J=7.1 Hz).

EXAMPLE 23

[1808] Production of Ethyl2-(4-benzoylaminophenyl)-1-cyclopentylbenzimidazole-5-carboxylate

[1809] Ethyl 1-cyclopentyl-2-(4-aminophenyl)benzimidazole-5-carboxylate(300 mg) obtained in Example 22 was dissolved in pyridine (3 ml) andchloroform (3 ml), and benzoyl chloride (127 mg) was added. The mixturewas stirred for 30 min at room temperature. The reaction mixture wasconcentrated under reduced pressure and water was added to the residueto allow crystallization. The crystals were collected by filtration togive the title compound (403 mg, yield 100%).

[1810]¹H-NMR (300 MHz, CDCl₃): 8.58 (1H, s), 8.00 (1H, d, J=9.0 Hz),7.84 (2H, d, J=7.5 Hz), 7.60-7.40 (6H, m), 7.14 (2H, d, J=7.5 Hz), 4.84(1H, quint, J=8.7 Hz), 4.41 (2H, q, J=7.5 Hz), 2.20-1.30 (8H, m), 1.41(3H, t, J=7.5 Hz).

EXAMPLE 24

[1811] Production of2-(4-benzoylaminophenyl)-1-cyclopentylbenzimidazole-5-carboxylic Acid

[1812] Ethyl2-(4-benzoylaminophenyl)-1-cyclopentylbenzimidazole-5-carboxylate (200mg) obtained in Example 23 was treated in the same manner as in Example2 to give the title compound (131 mg, yield 70%). melting point: notlower than 300° C.

[1813] FAB-Ms: 426 (MH+).

[1814]¹H-NMR (300 MHz, DMSO-d₆): 10.75 (1H, s), 8.35 (1H, s) 8.15 and7.85 (4H, ABq, J=8.9 Hz), 8.10-7.98 (4H, m), 7.70-7.55 (3H, m), 5.02(1H, quint, J=8.7 Hz), 2.36-2.15 (4H, m), 2.14-1.95 (2H, m), 1.80-1.62(2H, m).

EXAMPLE 25

[1815] Production of Ethyl2-{4-[3-(3-chlorophenyl)phenoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylate

[1816] Ethyl2-[4-(3-bromophenoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylate (65g) obtained in Example 1 and 3-chlorophenylboronic acid (23 g) weretreated in the same manner as in Example 5 to give the title compound(59 g, yield 85%).

[1817]¹H-NMR (300 MHz, CDCl₃): 8.51 (1H, d, J=1.8 Hz), 7.99 (1H, dd,J=8.7, 1.8 Hz), 7.71-7.55 (4H, m), 7.51-7.43 (2H, m), 7.43-7.27 (4H, m),7.19 (1H, d, J=8.4 Hz), 7.12 (1H, m), 4.41 (2H, q, J=7.2 Hz), 4.39 (1H,m), 2.42-2.22 (2H, m), 2.03-1.87 (4H, m), 1.79 (1H, m), 1.42 (3H, t,J=7.2 Hz), 1.39-1.29 (3H, m).

EXAMPLE 26

[1818] Production of2-{4-[3-(3-chlorophenyl)phenoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicAcid

[1819] Ethyl2-{4-[3-(3-chlorophenyl)phenoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylate(59 g) obtained in Example 25 was treated in the same manner as inExample 2 to give the title compound (43 g, yield 76%).

[1820] melting point: 253-254° C.

[1821] FAB-Ms: 523 (MH+).

[1822]¹H-NMR (300 MHz, DMSO-d₆): 12.82 (1H, brs) 8.24 (1H, d, J=1.3 Hz),7.98 (1H, d, J=8.7 Hz), 7.89 (1H, dd, J=8.7, 1.3 Hz), 7.78 (1H, s),-7.72 (2H, d, J=9.7 Hz), 7.70 (1H, m), 7.64-7.42 (5H, m), 7.25 (2H, d,J=8.7 Hz), 7.20 (1H, m), 4.33 (1H, m), 2.39-2.17 (2H, m), 2.00-1.76 (4H,m), 1.65 (1H, m), 1.50-1.22 (3H, m).

EXAMPLE 27

[1823] Production of Ethyl2-[4-(3-acetoxyphenyloxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylate

[1824] In the same manner as in Example 1, the title compound (87 g) wasobtained.

EXAMPLE 28

[1825] Production of Ethyl1-cyclohexyl-2-[4-(3-hydroxyphenyloxy)-phenyl]benzimidazole-5-carboxylate

[1826] Ethyl2-[4-(3-acetoxyphenyloxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylate(87 g) obtained in Example 27 was dissolved in methyl alcohol (250 ml)and tetrahydrofuran (250 ml), and potassium carbonate (31 g) was added.The mixture was stirred for 30 min at room temperature. The insolublematerials were filtered off and the filtrate was concentrated underreduced pressure. Water was added to the residues and the mixture wasneutralized with 2N hydrochloric acid. The precipitated crystals werecollected by filtration to give the title compound (78 g, yield 97%).

[1827]¹H-NMR (300 MHz, DMSO-d₆): 9.71 (1H, s), 7.98 (1H, d, J=8.7 Hz),7.87 (1H, d, J=8.7 Hz), 7.68 (2H, d, J=8.6 Hz), 7.24 (1H, t, J=8.1 Hz),7.18 (2H, d, J=8.6 Hz), 6.63 (1H, d, J=8.1 Hz), 6.57 (1H, d, J=8.1 Hz),6.51 (1H, s), 4.38-4.23 (1H, m), 4.35 (2H, q, J=6.9 Hz), 2.36-2.18 (2H,m), 1.99-1.78 (4H, m), 1.71-1.59 (1H, m), 1.45-1.20 (3H, m), 1.36 (3H,t, J=6.9 Hz).

EXAMPLE 29

[1828] Production of Ethyl1-cyclohexyl-2-{4-[3-(4-pyridylmethoxy)-phenyloxy]phenyl}benzimidazole-5-carboxylate

[1829] Ethyl1-cyclohexyl-2-[4-(3-hydroxyphenyloxy)phenyl]-benzimidazole-5-carboxylate(78 g) obtained in Example 28 was suspended in dimethylformamide (800ml), and sodium hydride (60% oil, 14 g) was added under ice-cooling. Themixture was stirred for 1 hr at room temperature. After the reactionmixture was ice-cooled, 4-chloromethylpyridine hydrochloride (29 g) wasadded and the mixture was stirred for 30 min. The mixture was thenstirred overnight at room temperature. Water was added to the reactionmixture and the precipitated crystals were collected by filtration. Theresulting crystals were recrystallized from ethyl alcohol to give thetitle compound (77 g, yield 82%).

[1830]¹H-NMR (300 MHz, CDCl₃): 8.63 (2H, d, J=6.0 Hz), 8.51 (11H, s),7.99 (1H, d, J=8.7 Hz), 7.66 (2H, d, J=8.7 Hz), 7.62 (2H, d, J=8.7 Hz),7.36 (2H, d, J=8.7 Hz), 7.31 (1H, t, J=8.2 Hz), 7.26 (1H, s), 7.16 (2H,d, J=8.7 Hz), 6.79-6.70 (3H, m), 5.09 (2H, s), 4.47-4.31 (1H, m), 4.42(2H, q, J=7.0 Hz), 2.42-2.22 (2H, m), 2.04-1.71 (5H, m), 1.45-1.25 (3H,m), 1.42 (3H, t, J=7.0 Hz).

EXAMPLE 30

[1831] Production of1-cyclohexyl-2-{4-[3-(4-pyridylmethoxy)phenyloxy]-phenyl}benzimidazole-5-carboxylicAcid

[1832] Ethyl1-cyclohexyl-2-{4-[3-(4-pyridylmethoxy)phenyloxy]-phenyl}benzimidazole-5-carboxylate(60 g) obtained in .Example 29 was treated in the same manner as inExample 2 to give the title compound (54 g, yield 75%).

[1833] melting point: 235-237° C.

[1834] FAB-Ms: 520 (MH+).

[1835]¹H-NMR (300 MHz, DMSO-d₆): 8.58 (2H, d, J=6.0 Hz), 8.23 (1H, s),7.96 and 7.86 (2H, ABq, J=8.7 Hz), 7.68 and 7.17 (4H, A′B′q, J=8.7 Hz),7.44 (2H, d, J=8.7 Hz), 7.39 (1H, t, J=8.3 Hz), 6.90 (1H, d, J=8.1 Hz),6.84 (1H, s), 6.75 (1H, d, J=8.1 Hz), 5.22 (2H, s), 4.40-4.22 (1H, m),2.40-2.19 (2H, m), 2.00-1.80 (4H, m).

EXAMPLE 241

[1836] Production of Methyl2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylate

[1837] Step 1: Production of 2-bromo-5-methoxybenzaldehyde

[1838] 3-Methoxybenzaldehyde (15 g) was dissolved in acetic acid (75ml), and a solution of bromine (5.7 ml) dissolved in acetic acid (15 ml)was added dropwise. The mixture was stirred overnight at roomtemperature and water (150 ml) was added to the reaction mixture. Theprecipitated crystals were collected by filtration, washed with waterand dried under reduced pressure to give the title compound (21 g, yield88%).

[1839]¹H-NMR (300 MHz, CDCl₃): 10.31 (1H, s), 7.52 (1H, d, J=8.8 Hz),7.41 (1H, d, J=3.3 Hz), 7.03 (1H, dd, J=8.8, 3.3 Hz), 3.48 (3H, s).

[1840] Step 2: Production of 2-(4-chlorophenyl)-5-methoxybenzaldehyde

[1841] 2-Bromo-5-methoxybenzaldehyde (10 g) obtained in the previousstep was treated in the same method as in Example 5 to give the titlecompound (11 g, yield 96%).

[1842]¹H-NMR (300 MHz, CDCl₃): 9.92 (1H, s), 7.50 (1H, d, J=2.6 Hz),7.48-7.14 (6H, m), 3.90 (3H, s).

[1843] Step 3: Production of 2-(4-chlorophenyl)-5-methoxybenzyl Alcohol

[1844] 2-(4-Chlorophenyl)-5-methoxybenzaldehyde (10 g) obtained in theprevious step was dissolved in tetrahydrofuran (30 ml). The solution wasadded dropwise to a suspension of sodium borohydride (620 mg) inisopropyl alcohol (50 ml) and the mixture was stirred for 1 hr. Thesolvent was evaporated under reduced pressure and water was added to theresidue. The precipitated crystals were collected by filtration anddried under reduced pressure. The resulting crystals were recrystallizedfrom a mixture of methanol and water to give the title compound (9.2 g,yield 91%).

[1845]¹H-NMR (300 MHz, CDCl₃): 7.37 (2H, d, J=8.6 Hz), 7.27 (2H, d,J=8.6 Hz), 7.17 (1H, d, J=8.6 Hz), 7.11 (1H, d, J=2.6 Hz), 6.89 (1H, dd,J=8.6, 2.6 Hz), 4.57 (2H, s), 3.86 (3H, s).

[1846] Step 4: Production of 2-(4-chlorophenyl)-5-methoxybenzyl Chloride

[1847] 2-(4-Chlorophenyl)-5-methoxybenzyl alcohol (20 g) obtained in theprevious step was dissolved in ethyl acetate (10 ml) and pyridine (0.5ml), and thionyl chloride (11 ml) was added dropwise. The mixture wasstirred for 1 hr. Water was added to the reaction mixture and themixture was extracted with ethyl acetate. The organic layer was washedwith water, saturated aqueous sodium hydrogencarbonate, water andsaturated brine, dried over anhydrous magnesium sulfate, andconcentrated under reduced pressure. Isopropyl alcohol was added to theresidue to allow crystallization. The resulting crystals were collectedby filtration and dried under reduced pressure to give the titlecompound (16 g, yield 74%).

[1848]¹H-NMR (300 MHz, CDCl₃): 7.43-7.29 (4H, m), 7.17 (1H, d, J=8.6Hz), 7.05 (1H, d, J=2.6 Hz), 6.96-6.89 (1H, m), 4.46 (2H, s), 3.86 (3H,s).

[1849] Step 5: Production of Methyl2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylate

[1850] 2-(4-Chlorophenyl)-5-methoxybenzyl chloride (4.0 g) obtained inthe previous step and methyl1-cyclohexyl-2-(4-hydroxyphenyl)-benzimidazole-5-carboxylate (5.0 g)obtained in the same manner as in Example 3 were treated in the samemanner as in Example 4 to give the title compound (6.0 g, yield 72%).

[1851]¹H-NMR (300 MHz, CDCl₃): 8.48 (1H, s), 8.00-7.93 (1H, m),7.68-7.62 (1H, m), 7.54 (2H, d, J=9.0 Hz), 7.41-7.16 (6H, m), 7.04-6.93(3H, m), 4.97 (2H, s), 4.36 (1H, m), 3.94 (3H, s), 3.87 (3H, s),2.39-2.21 (2H, m), 2.02-1.88 (4H, m), 1.85-1.45 (4H, m).

EXAMPLE 242

[1852] Production of2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicAcid Hydrochloride

[1853] Methyl2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylate(5.0 g) obtained in Example 241 was treated in the same manner as inExample 2 to give the title compound (5.1 g, yield 98%).

[1854] APCI-Ms: 568 (MH+).

[1855]¹H-NMR (300 MHz, DMSO-d₆): 8.30 (1H, d, J=1.4 Hz), 8.24 (1El, d,J=8.7 Hz), 8.03 (1H, d, J=8.7 Hz), 7.72 (2H, d, J=8.7 Hz), 7.51-7.39(4H, m), 7.34-7.18 (4H, m), 7.11-7.03 (1H, m), 5.08 (2H, s), 4.35 (1H,m), 3.83 (3H, m), 2.40-2.18 (2H, m), 2.10-1.96 (2H, m), 1.93-1.78 (2Hm),1.72-1.18 (4H, m).

EXAMPLE 243

[1856] Production of Ethyl2-{4-[3-(4-chlorophenyl)pyridin-2-ylmethoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylate

[1857] Step 1: Production of Methyl 3-hydroxypicolinate

[1858] 3-Hydroxypicolinic acid (1.0 g) was suspended in methanol (10 ml)and concentrated sulfuric acid (1.0 ml) was added. The mixture wasrefluxed under heating for 5 hr. The reaction mixture was ice-cooled,neutralized with saturated aqueous sodium hydrogencarbonate, andextracted with chloroform. The organic layer was washed with water andsaturated brine, and dried over anhydrous magnesium sulfate. The solventwas evaporated under reduced pressure to give the title compound (711mg, yield 64%).

[1859]¹H-NMR (300 MHz, CDCl₃): 10.63 (1H, s), 8.28 (1H, dd, J=3.7, 1.8Hz), 7.47-7.35 (2H, m), 4.06 (3H, s).

[1860] Step 2: Production of Methyl3-(trifluoromethylsulfonyloxy)-pyridine-2-carboxylate

[1861] Methyl 3-hydroxypicolinate (710 mg) obtained in the previous stepand triethylamine (0.77 ml) were dissolved in dichloromethane (7 ml),and trifluoromethanesulfonic anhydride (0.86 ml) was added underice-cooling. The reaction mixture was allowed to warm to roomtemperature and the mixture was stirred for 2 hr. Water was added to thereaction mixture and the mixture was extracted with ethyl acetate. Theorganic layer was washed with saturated brine and dried over anhydrousmagnesium sulfate. The solvent was evaporated under reduced pressure togive the title compound (1.2 g, yield 90%).

[1862]¹H-NMR (300 MHz, CDCl₃): 8.80-8.73 (1H, m), 7.75-7.70 (1H, m) 7.63(1H, dd, J=8.2, 4.5 Hz), 4.05 (3H, s).

[1863] Step 3: Production of Methyl3-(4-chlorophenyl)pyridine-2-carboxylate

[1864] Methyl 3-(trifluoromethylsulfonyloxy)pyridine-2-carboxylate (1.2g) obtained in the previous step was treated in the same manner as inExample 5 to give the title compound (728 mg, yield 69%).

[1865]¹H-NMR (300 MHz, CDCl₃): 8.73-8.66 (1H, m), 7.77-7.68 (1H, m) 7.49(1H, dd, J=7.8, 4.5 Hz), 7.46-7.37 (2H, m), 7.32-7.23 (2H, m), 3.80 (3H,s).

[1866] Step 4: Production of [3-(4-chlorophenyl)pyridin-2-yl]methanol

[1867] Methyl 3-(4-chlorophenyl)pyridine-2-carboxylate (720 mg) obtainedin the previous step was dissolved in tetrahydrofuran (10 ml) and thesolution was ice-cooled. Lithium aluminum hydride (160 mg) was added tothe solution and the mixture was stirred for 1 hr. To the reactionmixture were added successively water (1.6 ml), 15% sodium hydroxide(1.6 ml) and water (4.8 ml). The insoluble materials were filtered offand the filtrate was concentrated under reduced pressure. The residuewas purified by silica gel flash chromatography (developing solvent,n-hexane:ethyl acetate=1:1) to give the title compound (208 mg, yield32%).

[1868]¹H-NMR (300 MHz, CDCl₃): 8.60 (1H, dd, J=4.8, 1.5 Hz), 7.60-7.55(1H, m), 7.40-7.48 (2H, m), 7.29-7.36 (1H, m), 7.27-7.20 (3H, m), 4.63(2H, s).

[1869] Step 5: Production of Ethyl2-{4-[3-(4-chlorophenyl)pyridin-2-ylmethoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylate

[1870] [3-(4-Chlorophenyl)pyridin-2-yl]methanol (200 mg) obtained in theprevious step was dissolved in chloroform (3 ml), and thionyl chloride(0.13 ml) and pyridine (catalytic amount) were added. The mixture wasstirred for 1 hr at room temperature and concentrated under reducedpressure. The residue was dissolved in dimethylformamide (3 ml), andethyl 1-cyclohexyl-2-(4-hydroxyphenyl)benzimidazole-5-carboxylate (232mg) obtained in the same manner as in Example 3 and potassium carbonate(250 mg) were added. The mixture was stirred for 3 hr with heating at80° C. The reaction mixture was then allowed to cool. Water was addedand the mixture was extracted with ethyl acetate. The organic layer waswashed with water and saturated brine, dried over anhydrous magnesiumsulfate and concentrated under reduced pressure. The residue waspurified by silica gel flash chromatography (developing solvent,n-hexane:ethyl acetate=1:2) to give the title compound (246 mg, yield68%).

[1871]¹H-NMR (300 MHz, CDCl₃): 8.71 (1H, dd, J=4.7, 1.4 Hz), 8.49 (1H,d, J=2.1 Hz), 7.96 (1H, d, J=10.2 Hz), 7.71-7.62 (2H, m), 7.53 (2H, d,J=8.7 Hz), 7.45-7.34 (5H, m), 7.04 (2H, d, J=8.7 Hz), 5.14 (2H, s),4.48-4.29 (3H, m), 2.38-2.19 (2H, m), 2.02-1.22 (11H, m).

EXAMPLE 244

[1872] Production of Methyl2-[4-(2-bromo-5-tert-butoxycarbonyl-benzyloxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylate

[1873] Step 1: Production of tert-butyl 4-bromo-3-methylbenzoate

[1874] 4-Bromo-3-methylbenzoic acid (25 g) was suspended indichloromethane (200 ml), and oxalyl chloride (12 ml) finddimethylformamide (catalytic amount) were added. The mixture was stirredfor 2 hr at room temperature and the solvent wags evaporated underreduced pressure. The residue was dissolved in tetrahydrofuran (200 ml)and the solution was ice-cool(ed. To the solution was added dropwise asolution of potassium tert-butoxide dissolved in tetrahydrofuran (150ml) and the mixture was stirred for 30 min. Water was added to thereaction mixture and the mixture was extracted with ethyl acetate. Theorganic layer was washed with water and saturated brine, and dried overanhydrous magnesium sulfate. The solvent was evaporated under reducedpressure to give the title compound (27 g, yield 85%).

[1875]¹H-NMR (300 MHz, CDCl₃): 7.83 (1H, d, J=2.2 Hz), 7.67-7.53 (2H,m), 2.43 (3H, s), 1.58 (9H, s).

[1876] Step 2: Production of Methyl2-[4-(2-bromo-5-tert-butoxycarbonylbenzyloxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylate

[1877] tert-Butyl 4-bromo-3-methylbenzoate (7.0 g) obtained in theprevious step and methyl1-cyclohexyl-2-(4-hydroxyphenyl)-benzimidazole-5-carboxylate (6.3 g)obtained in the same manner as in Example 3 were treated in the samemanner as in Example 4 to give the title compound (8.8 g, yield 77%).

[1878]¹H-NMR (300 MHz, CDCl₃): 8.49 (1H, d, J=1.5 Hz), 8.21 (1H, d,J=2.1 Hz), 7.97 (1H, d, J=10.2 Hz), 7.82 (1H, d, J=10.2 Hz),7.71-7.5B(4H, m), 7.16 (2H, d, T=8.7 Hz), 5.23 (2H, s), 4.38 (1H, m),3.95 (3.H, s), 2.40-2.23 (2H, m), 2.04-1.90 (4H, m), 1.84-1.73 (1H, m),1.59 (9H, s), 1.44-1.27 (3H, m).

EXAMPLE 245

[1879] Production of Methyl2-{4-[5-tert-butoxycarbonyl-2-(4-chlorophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylate

[1880] Methyl2-[4-(2-bromo-5-tert-butoxycarbonylbenzyloxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylate(4.5 g) obtained in Example 244 was treated in the same manner as inExample 5 to give the title compound (3.6 g, yield 76%).

[1881]¹H-NMR (300 MHz, CDCl₃): 8.48 (1H, s), 8.27 (1H, d, J=1.8 Hz),8.04 (1H, dd, J=7.9, 1.5 Hz), 7.96 (1H, dd, J=7.0, 1.5 Hz), 7.65 (1H, d,J=8.6 Hz), 7.55 (2H, d, J=8.6 Hz), 7.43-7.32 (5H, m), 7.01 (2H, d, J=8.6Hz), 4.99 (2H, s), 4.43-4.29 (1H, m), 3.95 (3H, s), 2.41-2.21 (2H, m),2.02-1.89 (4H, m), 1.82-1.73 (1H, m), 1.62 (9H, s), 1.46-1.28 (3H, m).

EXAMPLE 246

[1882] Production of Methyl2-{4-[5-carboxy-2-(4-chlorophenyl)-benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylatehydrochloride

[1883] Methyl2-{4-[5-tert-butoxycarbonyl-2-(4-chlorophenyl)-benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylate(3.5 g) obtained in Example 245 was dissolved in dichloromethane (35ml), and trifluoroacetic acid (35 ml) was added. The mixture was stirredfor 1 hr at room temperature and the reaction mixture was concentratedunder reduced pressure. The residue was dissolved in ethyl acetate, and4N hydrochloric acid-ethyl acetate was added. The precipitated crystalswere collected by filtration and dried under reduced pressure to givethe title compound (3.3 g, yield 97%).

[1884]¹H-NMR (300 MHz, DMSO-d₆): 8.33 (1H, d, J=1.5 Hz), 8.29 (1H, s),8.24 (1H, d, J=1.8 Hz), 8.09-8.00 (2H, m), 7.74 (2H, d, J=3.6 Hz),7.61-7.44 (5H, m), 7.24 (2H, d, J=8.6 Hz), 5.19 (2H, s), 4.36 (1H, m),3.93 (3H, s), 2.37-1.21 (10H, m).

EXAMPLE 247

[1885] Production of Methyl2-{4-[2-(4-chlorophenyl)-5-methylcarbamoyl-benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylate

[1886] Methyl 2-{4-[5-carboxy-2-(4-chlorophenylbenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylate hydrochloride(400 mg) obtained in Example 246 was suspended in dichloromethane (5ml), and oxalyl chloride (0.08 ml) and dimethylformamide (catalyticamount) were added. The mixture was stirred for 2 hr at roomtemperature. The reaction mixture was concentrated under reducedpressure and the residue was dissolved in dichloromethane (5 ml). Theresulting solution was added dropwise to a mixed solution of 40% aqueousmethylamine solution (5 ml) and tetrahydrofuran (5 ml) underice-cooling. The reaction mixture was stirred for 1 hr and concentratedunder reduced pressure. Water was added to the residue and the mixturewas extracted with ethyl acetate. The organic layer was washed withwater, saturated aqueous sodium hydrogencarbonate and saturated brine,and dried over anhydrous magnesium sulfate. The solvent was evaporatedunder reduced pressure and the residue was crystallized from ethylacetate and diisopropyl ether. The crystals were collected by filtrationand dried under reduced pressure to give the title compound (335 mg,yield 86%).

[1887]¹H-NMR (300 MHz, CDCl₃): 8.47 (1H, s), 8.06 (1H, d, J=1.8 Hz),7.96 (1H, dd, J=8.6, 1.5 Hz), 7.82 (1H, dd, J=8.2, 2.2 Hz), 7.64 (-.H,d, J=8.6 Hz), 7.54 (2H, d, J=9.0 Hz), 7.44-7.31 (5H, m), 6.99 (2H, d,J=9.0 Hz), 6.35-6.26 (1H, m), 5.00 (2H, s), 4.35 (1H, m), 3.95 (3H, s),3.05 (3H, d, J=4.8 Hz), 2.40-1.24 (10H, m).

EXAMPLE 248

[1888] Production of2-{4-[2-(4-chlorophenyl)-5-methylcarbamoylbenzyloxyl]phenyl}-1-cyclohexylbenzimidaizole-5-carboxylateHydrochloride

[1889] Methyl2-{4-[2-(4-chlorophenyl)-5-methylcarbamoylbenzyloxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylate(150 mg) obtained in Example 247 and tetrahydrofuran (2 ml) were treatedin the same manner as in Example 2 to give the title compound (141 mg,yield 90%).

[1890] APCI-Ms: 594 (MH+).

[1891]¹H-NMR (300 MHz, DMSO-d₆) 8.65-8.58 (1H, m), 8.27 (1H, d, J=1.5Hz) 8.21 (1H, d, J=8.2 Hz), 8.15 (1H, d, J=1.5 Hz), 8.05-7.90 (2H, m),7.70 (2H, d, J=8.6 Hz), 7.56-7.43 (5H, m), 7.21 (2H, d, J=8.6 Hz), 5.14(2H, s), 4.34 (1H, m), 2.81 (3H, d, J=4.5 Hz), 2.39-1.19 (10H, m).

EXAMPLE 336

[1892] Production of Methyl2-[4-(2-bromo-5-nitrobenzyloxy)-2-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylate

[1893] Commercially available 2-bromo-5-nitrotoluene was dissolved incarbon tetrachloride (30 ml), and N-bromosuccinimide (2.9 g) andN,N′-azobisisobutyronitrile (228 mg) were added, which was followed byrefluxing under heating overnight. The reaction mixture was allowed tocool, water was added and the mixture was extracted with chloroform. Theorganic layer was dried over magnesium sulfate and concentrated underreduced pressure. The residue was dissolved in dimethylformamide! (30ml) and methyl2-(2-fluoro-4-hydroxyphenyl)-1-cyclohexylbenzimidazole-5-carboxylate(3.8 g) obtained in the same manner as in Example 3 and potassiumcarbonate (3.8 g) were added, which was followed by stirring at 80° C.for 1 hr. The reaction mixture was allowed to cool, water was added andthe mixture was extracted with ethyl acetate. The organic layer waswashed with water and saturated brine, dried over anhydrous magnesiumsulfate and concentrated under reduced pressure. The residue waspurified by silica gel flash chromatography (n-hexane:ethyl acetate=1:1)to give the title compound (3.7 g, yield 61%).

[1894]¹H-NMR (300 MHz, CDCl₃): 8.55-8.45 (2H, m), 8.15-8.05 (11H, m),7.99 (1H, dd, J=8.6 Hz, 1.5 Hz), 7.70-7.55 (2H, m), 7.05-6.85 (2H, m),5.24 (2H, s), 4.06 (1H, m), 3.95 (3H, s), 2.35-2.15 (2H, n), 2.05-1.85(4H, m), 1.80-1.70 (1H, m), 1.45-1.20 (3H, m).

EXAMPLE 337

[1895] Production of Methyl2-[4-{2-(4-chlorophenyl)-5-nitrobenzyloxy}-2-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylate

[1896] Methyl2-[4-(2-bromo-5-nitrobenzyloxy)-2-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylate(2.0 g) obtained in Example 336, 4-chlorophenylboronic acid (590 mg) andtetrakis(triphenylphosphine)palladium (396 mg) were suspended indimethoxyethane (40 ml), and saturated aqueous sodium hydrogencarbonatesolution (20 ml) was added, which was followed by refluxing underheating for 1 hr. The reaction mixture was allowed to cool, water wasadded and the mixture was extracted with chloroform. The organic layerwas dried over anhydrous magnesium sulfate and concentrated underreduced pressure. The residue was purified by silica gel flashchromatography (n-hexane:ethyl acatate=2:1) to give the title compound(1.9 g, yield 90%).

[1897]¹H-NMR (300 MHz, CDCl₃): 8.55 (1H, d, J=2.3 Hz), 8.49 (1H, d,J=1.4 Hz), 8.29 (1H, dd, J=8.4 Hz, 2.3 Hz), 7.98 (1H, dd, J=8.6 Hz, 1.5Hz), 7.60-7.30 (6H, m), 6.85-6.70 (2H, m), 5.03 (2H, s), 4.02 (1H, m),3.95 (3H, s), 2.35-2.10 (2H, m), 2.05-1.70 (5H, m), 1.40-1.20 (3H, m).

EXAMPLE 338

[1898] Production of Methyl2-[4-{5-amino-2-(4-chlorophenyl)benzyloxy}-2-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylate

[1899] Methyl2-[4-{2-(4-chlorophenyl)-5-nitrobenzyloxy}-2-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylate(1.9 g) obtained in Example 337 was suspended in ethanol (40 ml), andtin(II) chloride dihydrate (3.5 g) was added, which was followed byrefluxing under heating for 30 min. The reaction mixture wasconcentrated under reduced pressure, 4N sodium hydroxide was added andthe mixture was extracted with chloroform. The organic layer was washedwith 2N sodium hydroxide and water, dried over anhydrous magnesiumsulfate and concentrated under reduced pressure. Diisopropyl ether wasadded to the residue, and the precipitated crystals were collected byfiltration to give the title compound (1.5 g, yield 82%).

[1900]¹H-NMR (300 MHz, CDCl₃): 8.49 (1H, d, J=1.2 Hz), 7.98 (1H, dd,J=9.0, 1.5 Hz), 7.66 (1H, d, J=8.7 Hz), 7.49 (1H, t, J=8.4 Hz),7.40-7.20 (3H, m),7.13 (1H, d, J=8.1 Hz), 6.92 (1H, d, J=2.7 Hz),6.85-6.65 (4H, m), 4.92 (2H, s), 4.03 (1H, m), 3.95 (3H, s), 3.82 (2H,brs), 2.30-2.10 (2H, m), 2.05-1.80 (4H, m), 1.80-1.70 (1H, m), 1.40-1.10(3H, m).

EXAMPLE 339

[1901] Production of Methyl2-[4-{2-(4-chlorophenyl)-5-(2-oxopyrrolidin-1-yl)benzyloxy}-2-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylate

[1902] Methyl2-[4-{5-amino-2-(4-chlorophenyl)benzyloxy}-2-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylate(500 mg) obtained in Example 338 and triethylamine (0.14 ml) weredissolved in chloroform (5 ml), and commercially available chlorobutyrylchloride (0.1 ml) was added under ice-cooling, which was followed bystirring at room temperature for 3 hr. Water was added to the reactionmixture and the mixture was extracted with ethyl acetate. The organiclayer was washed with water and saturated brine, dried over anhydrousmagnesium sulfate and concentrated under reduced pressure. The residuewas dissolved in dimethylformamide (6 ml) and potassium carbonate (244mg) was added, which was followed by stirring at 80° C. for 1 hr. Thereaction mixture was allowed to cool, water was added and theprecipitated crystals were collected by filtration to give the titlecompound (502 mg, yield 89%).

[1903]¹H-NMR (300 MHz, CDCl₃): 4.89 (1H, d, J=1.5 Hz), 7.98 (1H, dd,J=8.6 Hz, 1.6 Hz), 7.72 (1H, d, J=2.2 Hz), 7.75-7.65 (2H, m), 7.49 (1H,t, =8.3 Hz), 7.45-7.20 (5H, m), 6.85-7.65 (2H, m), 4.99 (2H, s),4.10-3.85 (6H, m), 2.66 (2H, t, J=7.8 Hz), 2.30-2.15 (4H, m), 2.00-1.85(4H, m), 1.80-1.70 (1H, m), 1.45-1.20 (3H, m).

EXAMPLE 340

[1904] Production of2-[4-{2-(4-chlorophenyl)-5-(2-oxopyrrolidin-1-yl)benzyloxy}-2-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylicAcid Hydrochloride

[1905] Methyl2-[4-{2-(4-chlorophenyl)-5-(2-oxopyrrolidin-1-yl)benzyloxy}-2-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylate(200 mg) obtained in Example 339 was treated in the same manner as inExample 2 to give the title compound (182 mg, yield 87%).

[1906] Ms: 638 (M+1).

[1907]¹H-NMR (300 MHz, CDCl₃): 8.28 (1H, d, J=1.3 Hz), 8.10 (11H, d,J=8.7 Hz), 8.05-7.90 (2H, m), 7.77 (1H, dd, J=8.4 Hz, 2.2 Hz), 7.61 (1H,t, J=8.5 Hz), 7.55-7.35 (5H, m), 7.00-7.20 (2H, m), 5.09 (2H, s), 4.06(1H, m), 3.90 (2H, t, J=6.9 Hz), 2.60-2.45 (2H, m), 2.30-2.00 (4H, m),1.95-1.75 (4H, m), 1.70-1.55 (1H, m), 1.45-1.15 (3H, m).

[1908] In the same manner as in Examples 1-30, 241-248 and 336-340 andoptionally using other conventional methods, where necessary, thecompounds of Examples 31-240, 249-335, 341-446, 701-703 and 1001-1559were obtained. The chemical structures and properties are shown in Table1 to 177, 185 to 212, 219 to 221 and 225 to 260.

EXAMPLE 501

[1909] Production of Methyl2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-1-cyclohexyl-1H-indole-5-carboxylate

[1910] Step 1: Production of Methyl 3-bromo-4-cyclohexylaminobenzoate

[1911] 3-Bromo-4-fluorobenzoic acid (2.0 g) was dissolved in methanol(20 ml) and concentrated sulfuric acid (2 ml) was added. The mixture wasrefluxed for 3 hr. The reaction mixture was poured into ice-cold waterand extracted with ethyl acetate (50 ml). The organic layer was washedwith water (30 ml) and saturated brine (30 ml), and dried over sodiumsulfate. After filtration, the solvent was evaporated under reducedpressure. The residue was dissolved in dimethyl sulfoxide (20 ml) andcyclohexylamine (10.3 ml) was added. The mixture was stirred overnightat 120° C. The reaction mixture was poured into 10% aqueous citric acidsolution (100 ml) and extracted with ethyl acetate (100 ml). The organiclayer was washed with water (50 ml) and saturated brine (50 ml), anddried over sodium sulfate. After filtration, the solvent was evaporatedunder reduced pressure and the residue was purified by silica gel flashchromatography (developing solvent, n-hexane:ethyl acetate=10:1) to givethe title compound (2.6 g, yield 92%).

[1912]¹H-NMR (300 MHz, CDCl₃): 8.10 (1H, d, J=1.9 Hz), 7.83 (1H, dd,J=1.9 Hz, 8.6 Hz), 6.59 (1H, d, J=8.7 Hz), 4.73 (1H, brd, J=7.3 Hz),3.85 (3H, s), 3.38 (1H, m), 2.10-2.00 (2H, m), 1.90-1.20 (8H, m).

[1913] Step 2: Production of4′-chloro-2-(4-iodophenoxymethyl)-4-methoxybiphenyl

[1914] 4-Iodophenol (5.0 g) was dissolved in acetone (50 ml), andpotassium carbonate (4.7 g) and4′-chloro-2-chloromethyl-4-methoxybiphenyl (6.0 g) obtained in Example241, Step 4 were added. The mixture was refluxed for 10 hr. The reactionmixture was concentrated and 4N aqueous sodium hydroxide solution (50ml) was added. The precipitated crystals were collected by filtration,washed with water, and dried under reduced pressure to give the titlecompound (10.0 g, yield 98%).

[1915]¹H-NMR (300 MHz, CDCl₃): 7.52 (2H, d, J=8.9 Hz), 7.35 (2H, d,J=8.5 Hz), 7.27-7.20 (3H, m), 7.12 (1H, s), 6.95 (1H, d, J=8.5 Hz), 6.62(2H, d, J=8.9 Hz), 4.84 (2H, s), 3.85 (3H, s).

[1916] Step 3: Production of[4-(4′-chloro-4-methoxybiphenyl-2-ylmethoxy)phenylethynyl]trimethylsilane

[1917] 4′-Chloro-2-(4-iodophenoxymethyl)-4-methoxybiphenyl (7.0 g)obtained in the previous step was dissolved in acetonitrile (50 ml), andtrimethylsilylacetylene (2.3 g), tetrakis-(triphenylphosphine)palladiumcomplex (1.8 g), copper(I) iodide (0.6 g) and triethylamine (50 ml) wereadded. The mixture was stirred overnight at room temperature andconcentrated. Water (30 ml) was added and the mixture was extracted withethyl acetate (50 ml). The organic layer was washed with water (30 ml)and saturated brine (30 ml) and dried over sodium sulfate. Afterfiltration, the solvent was evaporated under reduced pressure and theresidue was purified by silica gel flash chromatography (developingsolvent, n-hexane:ethyl acetate=10:1) to give the title compound (5.1 g,yield 79%).

[1918]¹H-NMR (300 MHz, CDCl₃): 7.37 (2H, d, J=8.9 Hz), 7.34 (2H, d,J=8.2 Hz), 7.28-7.21 (3H, m), 7.13 (1H, s), 6.94 (1H, d, J=8.2 Hz), 6.75(2H, d, J=8.9 Hz), 4.87 (2H, s), 3.85 (3H, s), 0.23 (9H, s).

[1919] Step 4: Production of Methyl3-[4-(4′-chloro-4-methoxybiphenyl-2-ylmethoxy)phenylethynyl]-4-cyclohexylaminobenzoate

[1920][4-(4′-Chloro-4-methoxybiphenyl-2-ylmethoxy)phenvrlethynyl]-trimethylsilane(5.1 g) obtained in the previous step was dissolved in methanol (50 ml)and chloroform (50 ml), and potassium carbonate (2.5 g) was added. Themixture was stirred for 3 hr at room temperature and concentrated. Water(30 ml) was added and the mixture was extracted with ethyl acetate (50ml). The organic layer was washed with water (30 ml) and saturated brine(30 ml) and dried over sodium sulfate. After filtration, the solvent wasevaporated under reduced pressure to give white crystals (3.8 g). Thewhite crystals (2.3 g) were dissolved in acetonitrile (10 ml), andmethyl 3-bromo-4-cyclohexylaminobenzoate (1.0 g) obtained in Step 1,tetrakis(triphenylphosphine)palladium complex (0.4 g), copper(I) iodide(0.1 g) and triethylamine (10 ml) were added. The mixture was stirredovernight at 100° C. and concentrated under reduced pressure. Water (30ml) was added and the mixture was extracted with ethyl acetate (50 ml).The organic layer was washed with water (30 ml) and saturated brine (30ml), and dried over sodium sulfate. After filtration, the solvent wasevaporated under reduced pressure and the residue was purified by silicagel flash chromatography (developing solvent, n-hexane:ethylacetate=8:1) to give the title compound (0.9 g, yield 49%).

[1921]¹H-NMR (300 MHz, CDCl₃): 8.03 (1H, s), 7.84 (1H, d, J=8.7 Hz),7.42-7.22 (7H, m), 7.15(1H, s), 6.95 (1H, d, J=8.2 Hz), 6.85 (2H, d,J=8.8 Hz), 6.59 (1H, d, J=8.8 Hz), 5.07 (1H, brs), 4.91 (2H, s), 3.86(3H, s), 3.85 (3H, s), 3.42 (1H, m), 2.15-2.00 (2H, m), 1.80-1.20 (8H,m).

[1922] Step 5: Production of Methyl2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-1-cyclohexyl-1H-indole-5-carboxylate

[1923] Methyl3-[4-(4′-chloro-4-methoxybiphenyl-2-ylmethoxy)phenyl-ethynyl]-4-cyclohexylaminobenzoate(0.5 g) obtained in the previous step was dissolved inN,N-dimethylformamide (5 ml), and copper(I) iodide (0.17 g) was added.The mixture was refluxed for 3 hr at 180° C. The insoluble materialswere removed by filtration. Water (10 ml) was added and the mixture wasextracted with ethyl acetate (30 ml). The organic layer was washed withwater (10 ml) and saturated brine (10 ml), and dried over sodiumsulfate. After filtration, the solvent was evaporated under reducedpressure and the residue was purified by silica gel flash chromatography(developing solvent, n-hexane:ethyl acetate=8:1) to give the titlecompound (0.27 g, yield 55%).

[1924]¹H-NMR (300 MHz, CDCl₃): 8.34 (1H, s), 7.85 (1H, d, J=8.8 Hz),7.62 (1H, d, J=8.8 Hz), 7.40-7.18 (8H, m), 7.00-6.94 (3H, m), 6.48 (1H,s), 4.95 (2H, m), 4.18 (1H, m), 3.93 (3H, s), 3.88 (3H, s), 2.45-2.25(2H, m), 1.95-1.20 (8H, m).

EXAMPLE 502

[1925] Production of2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-1-cyclohexyl-1H-indole-5-carboxylicAcid

[1926] Methyl2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-1-cyclohexyl-1H-indole-5-carboxylate(0.27 g) obtained in Example 501 was treated in the same manner as inExample 2 to give the title compound (0.19 g, yield 71%).

[1927] APCI-Ms: 566 (MH+).

[1928]¹H-NMR (300 MHz, DMSO-d₆): 12.43 (11H, brs), 8.20 (11H, s), 7.79(11H, d, J=9.3 Hz), 7.72 (1H, d, J=9.0 Hz), 7.50-7.20 (8H, m), 7.07-7.03(3H, m), 6.53 (1H, s), 5.01 (2H, s), 4.13 (1H, m), 3.83 (3H, m),2.35-2.25 (2H, m), 1.85-1.10 (8H, m).

[1929] In the same manner as in Examples 501 and 502, and optionallyusing other conventional methods where necessary, the compound ofExample 503 was obtained. The chemical structure and properties areshown in Table 207.

EXAMPLE 601

[1930] Production of Ethyl2-(4-benzyloxyphenyl)-3-cyclohexylimidazo-[1,2-a]pyridine-7-carboxylate

[1931] Step 1: Production of 4-benzyloxy-N-methoxy-N-methylbenzamide

[1932] 4-Benzyloxybenzoic acid (5.0 g) and N,O-dimethyl-hydroxylaminehydrochloride (2.5 g) were suspended in dimethylformamide (50 ml), and1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (5.0 g),1-hydroxybenzotriazole (3.5 g) and triethylamine (3.6 ml) were added.The mixture was stirred overnight at room temperature. Water was addedto the reaction mixture and the mixture was extracted with ethylacetate. The organic layer was washed successively with water, saturatedaqueous sodium hydrogencarbonate, water and saturated brine, and driedover anhydrous magnesium sulfate. The solvent was evaporated underreduced pressure to give the title compound (5.6 g, yield 94%).

[1933]¹H-NMR (300 MHz, CDCl₃): 7.22, 2H, d, J=8.8 Hz), 7.28-7.46 (5H,m), 6.97 (2H, d, J=8.8 Hz), 5.10 (2H, s), 3.56 (3H, s), 3.35 (3w, s).Step 2: Production of 1-(4-benzyloxyphenyl)-2-cyclohexylethanoneMagnesium (470 mg) was suspended in tetrahydrofuran (2 ml) andcyclohexylmethyl bromide (3.4 g) was added dropwise at room temperature.After the addition, the reaction mixture was stirred for 30 min at 60°C. The reaction mixture was allowed to cool and diluted withtetrahydrofuran (5 ml). Separately,4-benzyloxy-N-methoxy-N-methylbenzamide (3.4 g) obtained in the previousstep was dissolved in tetrahydrofuran (10 ml) and the solution was addeddropwise to the reaction mixture at room temperature. The mixture wasstirred for 2 hr and saturated aqueous ammonium chloride solution wasadded to the reaction mixture. The mixture was extracted with diethylether. The organic layer was washed with saturated brine and dried overanhydrous magnesium sulfate, and the solvent was evaporated underreduced pressure. The residue was purified by silica gel flashchromatography (developing solvent, n-hexane:ethyl acetate=9:1) to givethe title compound (3.8 g, yield 66%).

[1934]¹H-NMR (300 MHz, CDCl₃): 7.93 (2H, d, J=8.8 Hz), 7.28-7.46 (5H,m), 7.00 (2H, d, J=8.8 Hz), 5.13 (2H, s), 2.76 (2H, d, J=6.8 Hz), 1.95(1H, m), 0.78-1.82 (10H, m).

[1935] Step 3: Production of1-(4-benzyloxyphenyl)-2-bromo-2-cyclohexylethanone

[1936] 1-(4-Benzyloxyphenyl)-2-cyclohexylethanone (1.0 g) obtained inthe previous step was dissolved in 1,4-dioxane (10 ml) and bromine (0.17ml) was added. The mixture was stirred for 10 min at room temperature.Saturated aqueous sodium hydrogencarbonate was added to the reactionmixture and the mixture was extracted with diethyl ether. The organiclayer was washed with water and saturated brine and dried over anhydrousmagnesium sulfate, and the solvent was evaporated under reducedpressure. The residue was purified by silica gel flash chromatography(developing solvent, n-hexane:ethyl acetate=9:1) to give the titlecompound (696 mg, yield 55%).

[1937]¹H-NMR (300 MHz, CDCl₃): 7.98 (2H, d, J=8.9 Hz), 7.28-7.4E(5H, m),7.02 (2H, d, J=8.9 Hz), 5.14 (2H, s), 4.89 (1H, d, J=9.3 Hz), 0.86-3.30(11H, m).

[1938] Step 4: Production of Ethyl2-(4-benzyloxyphenyl)-3-cyclohexylimidazo[1,2-a]pyridine-7-carboxylate

[1939] Ethyl 2-aminopyridine-4-carboxylate (214 mg) prepared accordingto JP-A-8-48651, 1-(4-benzyloxyphenyl)-2-bromo-2-cyclohexylethanone (500mg) obtained in the previous step and potassium carbonate (356 mg) werestirred for 5 hr with heating at 140° C. The reaction mixture wasallowed to cool and. chloroform was added. The insoluble materials werefiltered off and the filtrate was concentrated under reduced pressure.The residue was purified by silica gel flash chromatography (developingsolvent, n-hexane:ethyl acetate=1:1) to give the title compound (95 mg,yield 16%).

[1940] APCI-MS: 455 (MH+).

[1941]¹H-NMR (300 MHz, CDCl₃): 8.33 (1H, s), 8.21 (1H, d, J=7.5 Hz),7.55 (2H, d, J=8.7 Hz), 7.25-7.50 (6H, m), 5.13 (2H, s), 4.41 (2H, q,J=7.1 Hz), 3.25 (1H, m), 1.41 (3H, t, J=7.1 Hz), 1.15-2.00 (10H, m).

EXAMPLE 602

[1942] Production of2-(4-benzyloxyphenyl)-3-cyclohexylimidazo[1,2-a]pyridine-7-carboxylicAcid

[1943] Ethyl2-(4-benzyloxyphenyl)-3-cyclohexylimidazo[1,2-a]pyridine-7-carboxylate(95 mg) obtained in the previous step was treated in the same manner asin Example 2 to give the title compound (33 mg, 37%).

[1944] APCI-MS: 427 (MH+).

[1945]¹H-NMR (300 MHz, DMSO-d₆): 8.67 (11H, d, J=7.3 Hz), 8.08 (1H, s),7.25-7.58 (8H, m), 7.13 (2H, d, J=8.7 Hz), 5.17 (2H, s), 3.23 (1:r, m),1.25-2.10 (10H, m).

[1946] The compounds shown in Tables 213 to 218 can be further obtainedin the same manner as in Examples 1 to 701 or by other conventionalmethod employed as necessary.

[1947] The evaluation of the HCV polymerase inhibitory activity of thecompound of the present invention is explained in the following. Thispolymerase is an enzyme coded for by the non-structural protein regioncalled NS5B on the RNA gene of HCV (EMBO J., 15:12-22, 1996).

EXPERIMENTAL EXAMPLE [I]

[1948] i) Preparation of Enzyme (HCV Polymerase)

[1949] Using, as a template, a cDNA clone corresponding to the fulllength RNA gene of HCV BK strain obtained from the blood of a patientwith hepatitis C, a region encoding NS5B (591 amino acids; J Virol March1991, 65 (3), 1105-13) was amplified by PCR. The objective gene wasprepared by adding a 6 His tag {base pair encoding 6 continuoushistidine (His)} to the 5′ end thereof and transformed to Escherichiacoli. The Escherichia coli capable of producing the objective proteinwas cultured. The obtained cells were suspended in a buffer solutioncontaining a surfactant and crushed in a microfluidizer. The supernatantwas obtained by centrifugation and applied to various columnchromatographs {poly[U]-Sepharose, Sephacryl S-200, mono-S (Pharmacia)},inclusive of metal chelate chromatography, to give a standard enzymeproduct.

[1950] ii) Synthesis of Substrate RNA

[1951] Using a synthetic primer designed based on the sequence of HCVgenomic 3′ untranslated region, a DNA fragment (148 bp) containing polyUand 3′X sequence was entirely synthesized and cloned into plasmidpBluescript SK II(+) (Stratagene). The cDNA encoding full length NS5B,which was prepared in i) above, was digested with restriction enzymeKpnI to give a cDNA fragment containing the nucleotide sequence of fromthe restriction enzyme cleavage site to the termination codon. This cDNAfragment was inserted into the upstream of 3′ untranslated region of theDNA in pBluescript SK II (+) and ligated. The about 450 bp inserted DNAsequence was used as a template in the preparation of substrate RNA.This plasmid was cleaved immediately after the 3′X sequence, linearizedand purified by phenol-chloroform treatment and ethanol precipitation togive DNA.

[1952] RNA was synthesized (37° C., 3 hr) by run-off method using thispurified DNA as a template, a promoter of pBluescript SK II(+),MEGAscript RNA synthesis kit (Ambion) and T7 RNA polymerase. DNaseI wasadded and the mixture was incubated for 1 hr. The template DNA wasremoved by decomposition to give a crude RNA product. This product wastreated with phenol-chloroform and purified by ethanol precipitation togive the objective substrate RNA.

[1953] This RNA was applied to formaldehyde denaturation agarose gelelectrophoresis to confirm the quality thereof and preserved at −80° C.

[1954] iii) Assay of Enzyme (HCV Polymerase) Inhibitory Activity

[1955] A test substance (compound of the present invention) and areaction mixture (30 μl) having the following composition were reactedat 25° C. for 90 min. 10% Trichloroacetic acid at 4° C. and 1% sodiumpyrophosphate solution (150 μl) were added to this reaction mixture tostop the reaction. The reaction mixture was left standing in ice for 15min to insolubilize RNA. This RNA was trapped on a glass filter (WhatmanGF/C and the like) upon filtration by suction. This filter was washedwith a solution containing 1% trichloroacetic acid and 0.1% sodiumpyrophosphate, washed with 90% ethanol and dried. A liquid scintillationcocktail (Packard) was added and the radioactivity of RNA synthesized bythe enzyme reaction was measured on a liquid scintillation counter.

[1956] The HCV polymerase inhibitory activity (IC₅₀) of the compound ofthe present invention was calculated from the values of radioactivity ofthe enzyme reaction with and without the test substance.

[1957] The results are shown in Tables 178-184 and 222-224.

[1958] Reaction mixture: HCV polymerase (5 μg/ml) obtained in i),substrate RNA (10 μg/ml) obtained in ii), ATP (50 μM), GTP (50 μM), CTP(50 μM), UTP (2 μM), [5,6-³H]UTP (46 Ci/mmol (Amersham), 1.5 μCi) 20 mMTris-HCl (pH 7.5), EDTA (1 mM), MgCl₂(5 mM), NaCl (50 mM), DTT (1 mM),BSA (0.01%). TABLE 1 Example No. 31

1H NMR (δ) ppm 300MHz, CDCl3 7.81(2H, d, J=6.6Hz), 7.60(2H, d, J=8.8Hz),7.51-7.21(8H, m), 7.11(2H, d, J=8.8Hz), 5.15 (2H, s), 4.93(1H, quint,J=8.8Hz), 2.36-2.32(2H, m), 2.09-2.04(3H, m), 1.75-1.68(3H, m). Purity >90% (NMR) MS 369(M + 1) Example No. 32

1H NMR(δ) ppm 300MHz, CDCl3 8.51(1H, d, J=1.5Hz), 7.98(1H, d, J=8.4Hz),7.61(2H, d, J=8.7Hz), 7.56-7.10(6H, m), 7.12 (2H, d, J=8.7Hz), 5.15 (2H,s), 4.94(1H, quint, J=9.3Hz), 4.41(2H, q, J=7.5Hz), 2.40-1.50(8H, m),1.41(3H, t, J=7.5Hz) Purity > 90% (NMR) MS 441(M + 1) Example No. 33

1H NMR(δ) ppm 300MHz, CDCl3 7.84(1H, s), 7.61(2H, d, J=9.0Hz),7.58-7.30(7H, m), 7.12 (2H, d, J=9.0Hz), 5.15(2H, s), 4.94(1H, quint,J=8.7Hz), 3.10(6H, brs), 2.40-1.50(8H, m) Purity > 90% (NMR) MS 440(M +1)

[1959] TABLE 2 Example No. 34

1H NMR(δ) ppm 300MHz, CDCl3 8.20(1H, s), 7.50-7.31(9H, m), 7.12(2H, d,J=8.7Hz), 5.15 (2H, s), 4.94(1H, quint, J=8.7Hz), 3.61(3H, s), 3.40(3H,s), 2.41-1.42(8H, m) Purity > 90% (NMR) MS 456(M + 1) Example No. 35

1H NMR(δ) ppm 300MHz, CDCl3 7.91(1H, s), 7.59(2H, d, J=8.7Hz),7.49-7.30(7H, m), 7.11 (2H, d, J=8.8Hz), 5.15(2H, s), 4.19(1H, quint,J=8.8Hz), 2.41-2.22(2H, m), 2.13-1.49(14H, m) Purity > 90% (NMR) MS427(M + 1) Example No. 36

1H NMR(δ) ppm 300MHz, CDCl3 8.40(1H, d, J=1.4Hz), 7.95 (1H, dd, J=8.6,1.4Hz), 7.61(2H, d, J=8.7Hz), 7.57-7.30(6H, m), 7.13(2H, d, J=8.7Hz),5.16(2H, s), 4.95(1H, quint, J=8.8Hz), 2.64(3H, s), 2.40-1.54(8H, m)Purity > 90% (NMR) MS 411(M + 1)

[1960] TABLE 3 Example No. 37

1H NMR(δ) ppm 300MHz, DMSO-d6 10.47(1H, brs,), 9.15(1H, brs), 8.40(1H,s), 8.07(1H, d, J=9.0Hz), 7.93(1H, d, J=8.7Hz), 7.77(2H, d, J=8.7Hz),7.55-7.29(7H, m), 5.26(2H, s), 4.93 (1H, quint, J=9.0Hz), 3.77-3.63(2H,m), 3.39-3.23 (2H, m), 2.84(6H, d, J=4.8Hz), 2.32-1.60(8H, m) Purity >90% (NMR) MS 483(M + 1) Example No. 38

1H NMR(δ) ppm 300MHz, CDCl3 8.69(1H, s), 8.19(1H, d, J=9.0Hz), 7.62(2H,d, J=8.7Hz), 7.54(1H, d, J=9.0Hz), 7.48-7.36(5H, m), 7.15(2H, d,J=8.7Hz), 5.17(2H, s), 4.98(1H, quint, J=9.0Hz), 2.27-2.07 (6H, m),1.82-1.78(2H, m). Purity > 90% (NMR) MS 414(M + 1) Example No. 39

1H NMR(δ) ppm 300MHz, DMSO-d6 7.84(1H, d, J=9.0Hz), 7.79(2H, d,J=8.7Hz), 7.52-7.33(8H, m), 7.26(1H, d, J=9.0Hz), 5.27(2H, s), 4.92(1H,quint, J=9.3Hz), 2.19-1.70(8H, m). Purity > 90% (NMR) MS 384(m + 1)

[1961] TABLE 4 Example No. 40

1H NMR(δ) ppm 300MHz, CDCl3 7.72(1H, s), 7.60-7.35(10H, m), 7.10(2H, d,J=8.7Hz), 5.14(2H, s), 4.90(1H, quint, J=8.8Hz), 2.29-2.19(2H, m),2.19(3H, s), 2.19-1.74(6H, m). Purity > 90% (NMR) MS 426(M + 1) ExampleNo. 41

1H NMR(δ) ppm 300MHz, CDCl3 7.66(1H, s), 7.61(2H, d, J=8.8Hz),7.50-7.28(7H, m), 7.12 (2H, d, J=8.8Hz), 6.86(1H, brs), 5.15(2H, s),4.94(1H, quint, J=8.8Hz), 2.97(3H, s), 2.29-1.76(8H, m). Purity > 90%(NMR) MS 462(M + 1) Example No. 42

1H NMR(δ) ppm 300MHz, DMSO 8.11(1H, s), 7.81(1H, d, J=8.4Hz), 7.72(1H,d, J=8.4Hz), 7.65(2H, d, J=8.4Hz), 7.51(2H, m), 7.43(2H, m), 7.37(1H,m), 7.29(2H, s), 7.23(2H, d, J=8.4Hz), 5.22(2H, s), 4.89(1H, quintet,J=9.2Hz), 2.12-2.0(6H, m), 1.7(2H, m). Purity > 90% (NMR) MS 448(M+)

[1962] TABLE 5 Example No. 43

1H NMR(δ) ppm 300MHz, DMSO-d6 8.33(1H, s), 8.08(1H, d, J=9.0Hz),7.99(1H, d, J=9.0Hz), 7.47-7.41(4H, m), 7.33(2H, d, J=8.4Hz), 5.22(2H,s), 4.96 (1H, quint, J=9.0Hz), 2.25-1.60(8H, m), 1.30(9H, s) Purity >90% (NMR) MS 469(M + 1) Example No. 44

1H NMR(δ) ppm 300MHz, DMSO-d6 12.9(2H, brs), 8.25(1H, s), 8.00(2H, d,J=7.8Hz), 7.90(1H, d, J=8.4Hz), 7.74(1H, d, J=8.7Hz), 7.67(2H, d, J=9.0Hz), 7.62(2H, d, J=8.1Hz), 7.24 (2H, d, J=8.4Hz), 5.32(2H, s), 4.88(1H,quint, J=9.0 Hz, 2.25-1.60(8H, m). Purity > 90% (NMR) MS 457(M + 1)Example No. 45

1H NMR(δ) ppm 300MHz, DMSO-d6 13.4(1H, brs), 8.32(1H, s), 8.06(1H, d,J=8.7Hz), 7.97(1H, d, J=8.7Hz), 7.79(2H, d, J=8.8Hz), 7.56-7.48(4H, m),7.33(2H, d, J=8.8Hz), 5.27 (2H, s), 4.95(1H, quint, J=8.9Hz),2.30-1.60(8H, m). Purity > 90% (NMR) MS 447(M + 1)

[1963] TABLE 6 Example No. 46

1H NMR(δ) ppm 300MHz, DMSO-d6 8.33(1H, s), 8.07(1H, d, J=8.7Hz),7.98(1H, d, J=8.7Hz), 7.80(2H, d, J=8.4Hz), 7.34 (2H, d, 8.4Hz),7.19(1H, d, J=3.6Hz), 7.09(1H, d, J=3.6Hz), 5.41(2H, s), 4.95(1H, quint,J=8.7Hz), 2.30-1.60(8H, m). Purity > 90%(NMR) MS 453(M + 1) Example No.47

1H NMR(δ) ppm 300MHz, DMSO-d6 8.33(1H, s), 8.07(1H, d, J=8.4Hz),7.98(1H, d, J=9.0Hz), 7.82-7.72(6H, m), 7.35(2H, d, J=9.0Hz), 5.40(2H,s), 4.95 (1H, quint, J=8.7Hz), 2.35-1.60(8H, m). Purity > 90% (NMR) MS481(M + 1) Example No. 48

1H NMR(δ) ppm 300MHz, DMSO-d6 8.23(1H, s), 7.88(1H, d, J=8.4Hz),7.70(1H, d, J=8.4Hz), 7.64(2H, d, J=8.4Hz), 7.43 (2H, d, J=8.4Hz),7.20(2H, d, J=8.4Hz), 6.98(2H, d, J=8.4Hz), 5.13(2H, s), 4.88(1H, quint,J=8.7Hz), 3.77(3H, s), 2.35-1.60(8H, m). Purity > 90% (NMR) MS 443(M +1)

[1964] TABLE 7 Example No. 49

1H NMR(δ) ppm 300MHz, DMSO-d6 8.93(2H, d, J=6.6Hz), 8.35(1H, s),8.06-8.04(3H, m), 7.97 (1H, d, J=8.7Hz), 7.83(2H, d, J=8.7Hz), 7.38(2H,d, J=8.7Hz), 5.61(2H, s), 4.94(1H, quint, J=8.7Hz), 2.40-1.60(8H, m).Purity > 90% (NMR) MS 414(M + 1) Example No. 50

1H NMR(δ) ppm 300MHz, DMSO-d6 8.33(1H, s), 8.08(1H, d, J=8.7Hz),7.99(1H, d, J=9.0Hz), 7.78(2H, d, J=8.4Hz), 7.39(2H, d, J=8.1Hz),7.32(2H, d, J=8.7Hz), 7.23(2H, d, J=7.8Hz), 5.22(2H, s), 4.96(1H, quint,J=9.0Hz), 2.32(3H, s), 2.30-1.60(8H, m). Purity > 90% (NMR) MS427(M + 1) Example No. 51

1H NMR(δ) ppm 300MHz, DMSO-d6 8.31(1H, s), 8.03(1H, d, J=9.0Hz),7.93(1H, d, J=9.0Hz), 7.77(2H, d, J=8.4Hz), 7.31 (2H, d, J=8.7Hz),5.07(2H, s), 4.94(1H, quint, J=8.7Hz), 2.45(3H, s), 2.26(3H, s),2.26-1.60(8H, m). Purity > 90% (NMR) MS 432(M + 1)

[1965] TABLE 8 Example No. 52

1H NMR(δ) ppm 300MHz, DMSO-d6 12.7(1H, brs), 10.0(1H, s), 8.22(1H, s),7.87(1H, d, J=8.6Hz), 7.69(1H, d, J=8.6Hz), 7.53(2H, d, J=8.6Hz), 6.96(2H, d, J=8.6Hz), 4.89(1H, quint, J=9.0Hz), 2.30-1.60(8H, m). Purity >90% (NMR) MS 323(M + 1) Example No. 53

1H NMR(δ) ppm 300MHz, DMSO-d6 9.18(1H, t, J=5.6Hz), 8.34(1H, s),8.04(1H, d, J=9.6Hz), 7.98(1H, d, J=8.7Hz), 7.80 (2H, d, J=8.7Hz),7.52-7.32 (7H, m), 5.27(2H, s), 4.95(1H, quint, J=9.0Hz), 3.99(2H, d,J=5.7Hz), 2.40-1.60(8H, m). Purity > 90% (NMR) MS 470(M + 1) Example No.54

1H NMR(δ) ppm 300MHz, DMSO-d6 8.32(1H, s), 8.05(1H, d, J=8.7Hz),7.95(1H, d, J=8.7Hz), 7.80(2H, d, J=8.4Hz), 7.67 (1H, t, J=4.5Hz),7.56(1H, t, J=4.5Hz), 7.45-7.42(2H, m), 7.35(2H, d, J=8.4Hz), 5.31 (2H,s), 4.96(1H, quint, J=9.0Hz), 2.30-1.60(8H, m). Purity > 90% (NMR) MS447(M + 1)

[1966] TABLE 9 Example No. 55

1H NMR(δ) ppm 300MHz, DMSO-d6 12.78(1H, brs), 8.24(1H, s), 7.88 and 7.72(2H, ABq, J=8.6Hz), 7.66 and 7.23(4H, A′B′q, J=8.6Hz), 7.58(1H, s),7.48-7.42(3H, m), 5.24(1H, s), 4.88(1H, quint, J=8.8Hz), 2.30-1.91(6H,m), 1.78-1.60(2H, m) Purity > 90% (NMR) MS 447(M + 1) Example No. 56

1H NMR(δ) ppm 300MHz, DMSO 12.89(1H, broad), 8.18(1H, s), 7.87(1H, d,J=8.4Hz), 7.74 (1H, d, J=9.2Hz), 7.67(2H, d, J=8.8Hz), 7.52(2H, m), 7.45(2H, m), 7.38(1H, m), 7.23 (2H, d, J=8.8Hz), 5.22(2H, s), 4.94(1H,quintet, J=8.9Hz), 2.16(4H, m), 1.98(2H, m), 1.73(2H, m). Purity > 90%(NMR) MS 413(M+) Example No. 57

1H NMR(δ) ppm 300MHz, DMSO-d6 10.99(1H, s), 8.26(1H, s), 8.01-7.86(4H,m), 7.69-7.59(5H, m), 7.38(2H, d, J=8.7Hz), 4.86(1H, quint, J=8.7Hz),2.12-1.90(6H, m), 1.72-1.59 (2H, m) Purity > 90% (NMR) MS 462(M + 1)

[1967] TABLE 10 Example No. 58

1H NMR(δ) ppm 300MHz, DMSO-d6 12.78(1H, s), 10.69(1H, s), 8.26-7.72(9H,m), 4.92(1H, quint, J=9.0Hz), 2.34-1.70 (6H, m), 1.75-1.61(2H, m)Purity > 90% (NMR) MS 494(M + 1) Example No. 59

1H NMR(δ) ppm 300MHz, DMSO-d6 10.82(1H, s), 8.34(1H, s), 8.14 and7.84(4H, ABq, J=8.4Hz), 8.06 and 7.66(4H, A′B′q, J=8.6Hz), 8.06-7.98(4H,m), 5.01(1H, quint, J=9.3Hz), 2.35-2.15(4H, m), 2.11-1.96 (2H, m),1.80-1.62(2H, m) Purity > 90% (NMR) MS 460(M + 1) Example No. 60

1H NMR(δ) ppm 300MHz, DMSO-d6 10.61(1H, s), 8.32(1H, s), 8.12 and7.81(4H, ABq, J=8.9Hz), 8.03 and 7.93(2H, A′B′q, J=8.7Hz), 7.95 and7.59(4H, A″B″q, J=8.4Hz), 4.99(1H, quint, J=9.0Hz), 2.33-2.12(4H, m),2.10-1.93(2H, m), 1.80-1.63 (2H, m), 1.34(9H, m) Purity > 90% (NMR) MS482(M + 1)

[1968] TABLE 11 Example No. 61

1H NMR(δ) ppm 300MHz, DMSO-d6 10.6(1H, s), 8.34(1H, s), 8.13 (2H, d,J=8.7Hz), 8.09-7.98 (4H, m), 7.82(2H, d, J=8.7Hz), 7.50-7.35(5H, m),7.20-7.17 (2H, d, J=9.0Hz), 5.24 (2H, s), 5.01(1H, quint, J=9.3Hz),2.40-1.60(8H, m). Purity > 90% (NMR) MS 532(M + 1) Example No. 62

1H NMR(δ) ppm 300MHz, DMSO-d6 8.32(1H, s), 8.26(1H, d, J=8.7Hz),8.04(1H, d, J=8.7Hz), 7.77 (2H, d, J=8.4Hz), 7.52 (2H, d, J=6.9Hz),7.46-7.39 (5H, m), 5.28(2H, s), 4.38(1H, m), 3.71(1H, m), 2.60-2.15 (2H,m), 2.04-1.96(4H, m), 1.30-1.20(2H, m). Purity > 90% (NMR) MS 443(m + 1)Example No. 63

1H NMR(δ) ppm 300MHz, DMSO-d6 8.27(1H, s), 8.14(1H, d, J=8.7Hz),7.96(1H, d, J=8.4Hz), 7.71(2H, d, J=9.0Hz), 7.51 (2H, d, J=6.9Hz),7.46-7.37 (3H, m), 7.30(2H, d, J=8.4Hz), 5.25(3H, s), 4.39(1H, m),3.44(1H, m), 3.27(3H, s), 2.60-1.95 (6H, m), 1.25-1.05(2H, m). Purity

90% (NMR) MS 457(M + 1)

[1969] TABLE 12 Example No. 64

1H NMR(δ) ppm 300MHz, DMSO-d6 12.25(1H, brs), 7.70-7.30 (9H, m),7.20(2H, d, J=8.7Hz), 7.14(1H, d, J=8.4Hz), 5.20 (2H, s), 4.84(1H,quint, J=6.0Hz), 3.66(2H, s), 2.30-1.51(8H, m) Purity > 90% (NMR) MS427(M + 1) Example No. 65

1H NMR(δ) ppm 300MHz, DMSO-d6 12.64(1H, brs), 8.13(1H, s), 7.80(1H, d,J=7.2Hz), 7.59 (1H, d, J=8.7Hz), 7.48-7.30 (5H, m), 5.11(2H, s),5.03(1H, quint, J=8.7Hz), 4.20-4.05 (2H, m), 3.45-3.90(3H, m),2.15-1.60(12H, m) Purity > 90% (NMR) MS 448(M + 1) Example No. 66

1H NMR(δ) ppm 300MHz, DMSO-d6 10.59(1H, s), 8.31 (1H, s), 8.10(2H, d,J=8.6Hz), 8.03(1H, d, J=8.7Hz), 8.00-7.85(3H, m), 7.80(2H, d, J=8.6Hz),7.41(2H, d, J=8.2Hz), 4.98(1H, quint, J=8.8Hz), 2.71-1.10(19H, m)Purity > 90% (NMR) MS 508(M + 1)

[1970] TABLE 13 Example No. 67

1H NMR(δ) ppm 300MHz, DMSO-d6 12.81(1H, brs), 8.42(1H, s), 7.90(1H, d,J=8.5Hz), 7.80-7.52 (6H, m), 7.44(2H, d, J=8.6Hz), 5.25 (2H, s),4.88(1H, quint, J=8.8Hz), 2.30-1.52(8H, m) Purity > 90% (NMR) MS481(M + 1) Example No. 68

1H NMR(δ) ppm 300MHz, DMSO-d6 8.31(1H, d, J=1.4Hz), 8.05(1H, d,J=8.6Hz), 7.96(1H, d, J=8.6Hz), 8.86-8.61(4H, m), 7.51(1H, d, J=6.3Hz),7.33 (2H, d, J=8.8Hz), 5.28(2H, s), 4.94(1H, quint, J=8.8Hz),2.31-1.60(8H, m) Purity > 90% (NMR) MS 481(M + 1) Example No. 69

1H NMR(δ) ppm 300MHz, DMSO-d6 9.88(1H, s), 9.42(1H, s), 8.32 (1H, s),8.09 and 8.02(2H, ABq, J=9.0Hz), 7.81 and 7.78 (4H, A′B′q, J=9.2Hz),7.50(2H, d, J=7.8Hz), 7.31(2H, t, J=7.8Hz), 7.00(1H, t, J=7.8 Hz),5.03(1H, quint, J=8.7Hz), 2.34-2.17(4H, m), 2.13-1.96(2H, m),1.83-1.64(2H, m) Purity > 90% (NMR) MS 441(M + 1)

[1971] TABLE 14 Example No. 70

1H NMR(δ) ppm 300MHz, DMSO-d6 8.27(1H, d, J=1.2Hz), 8.04(1H, d,J=8.7Hz), 7.94(1H, d, J=8.7Hz), 7.72(2H, d, J=8.7 Hz), 7.60-7.20(12H, m)6.74 (1H, s), 4.92(1H, quint, J=8.9Hz), 2.30-1.58(8H, m) Purity > 90%(NMR) MS 489 (M + 1) Example No. 71

1H NMR(δ) ppm 300MHz, DMSO-d6 8.31(1H, s), 8.05(1H, d, J=8.7Hz),7.97(1H, d, J=8.7Hz), 7.76(2H, d, J=8.6Hz), 7.44-7.19(7H, m), 4.94(1H,quint, J=8.8Hz), 4.35(2H, t, J=6.7 Hz), 3.10(2H, t, J=6.7Hz),2.32-1.60(8H, m) Purity > 90% (NMR) MS 427(M + 1) Example No. 72

1H NMR(δ) ppm 300MHz, DMSO-d6 8.30(1H, s), 8.25(1H, d, J=8.7 Hz),8.03(1H, d, J=9.0Hz), 7.75(2H, d, J=8.7Hz), 7.51 (2H, d, J=7.2Hz),7.46-7.33 (5H, m), 5.27(2H, s), 4.36(1H, m), 2.50-2.25(2H, m),2.15-2.00(2H, m), 1.95-1.85(2H, m), 1.35(1H, m), 1.20-1.10 (2H, m),0.87(9H, s). Purity > 90% (NMR) MS 483(M + 1)

[1972] TABLE 15 Example No. 73

1H NMR(δ) ppm 300MHz, DMSO-d6 7.59(2H, d, J=8.4Hz), 7.52-7.35(6H, m),7.20(2H, d, J=8.7Hz), 7.14(1H, d, J=2.1Hz), 6.90(1H, dd, J=9.0, 2.4Hz),5.21(2H, s), 4.83(1H, quint, J=8.7Hz), 4.70(2H, s), 2.30-1.90(6H, m),1.75-1.55(2H, m). Purity > 90% (NMR) MS 443(M + 1) Example No. 74

1H NMR(δ) ppm 300MHz, DMSO-d6 8.27(1H, s), 8.06 and 7.97(2H, ABq,J=8.7Hz), 7.57 and 6.86 (4H, A′B′q, J=8.9Hz), 7.42-7.26(5H, m), 5.04(1H,quint, J=9.0Hz), 4.42(2H, s), 2.32-1.94(6H, m), 1.80-1.62 (2H, m)Purity > 90% (NMR) MS 412(M + 1) Example No. 75

1H NMR(δ) ppm 300MHz, DMSO-d6 12.80(1H, s), 8.26(1H, s), 7.90 (1H, d,J=9.2Hz), 7.76-7.60 (8H, m), 7.35(2H, d, J=8.4 Hz), 4.84(1H, quint,J=8.8Hz), 3.23(3H, s), 2.32-1.90 (6H, m), 1.78-1.61(2H, m) Purity > 90%(NMR) MS 476(M + 1)

[1973] TABLE 16 Example No. 76

1H NMR(δ) ppm 300MHz, DMSO-d6 8.29(1H, s), 8.07 and 7.49(2H, ABq,J=8.7Hz), 7.66 and 7.00 (4H, A′B′q, J=7.7Hz), 7.39-7.24(5H, m), 5.05(1H,quint, J=8.8Hz), 4.76(2H, s), 3.21 (3H, s), 2.35-1.92(6H, m),1.81-1.62(2H, m) Purity > 90% (NMR) MS 426(M + 1) Example No. 77

1H NMR(δ) ppm 300MHz, DMSO-d6 8.21(1H, s), 7.87(1H, s), 7.56 and7.43(4H, ABq, J=8.1Hz), 7.34-7.16(5H, m), 4.25(1h, brt, J=12.5Hz),3.06-2.92 (4H, m), 2.41-2.17(2H, m), 1.96-1.77(4H, m), 1.72-1.58 (1H,m), 1.48-1.15(3H, m) Purity > 90% (NMR) MS 425(M + 1) Example No. 78

1H NMR(δ) ppm 300MHz, DMSO-d6 8.14(1H, s), 7.79(1H, d, J=9.0 Hz),7.57(1H, d, J=8.7Hz), 7.40-7.20(5H, m), 4.89(1H, quint, J=8.7Hz),3.54(2H, s), 3.19-2.90(3H, m), 2.23-1.69(14H, m) Purity > 90% (NMR) MS404(M + 1)

[1974] TABLE 17 Example No. 79

1H NMR(δ) ppm 300MHz, DMSO-d6 8.15(1H, s), 7.81(1H, d, J=8.4 Hz),7.59(1H, d, J=9.0Hz), 7.50-7.38(5H, m), 5.05(1H, quint, J=9.0Hz),3.85-2.95 (3H, m), 2.20-1.65(14H, m) Purity > 90% (NMR) MS 418(M + 1)Example No. 80

1H NMR(δ) ppm 300MHz, DMSO-d6 8.17(1H, m), 7.84(1H, d, J=8.4 Hz),7.78-7.62(3H, m), 7.49 (2H, d, J=8.1Hz), 5.05-4.91 (1H, m),3.80-3.70(2H, m), 3.30-3.12(1H, m), 2.48-2.31 (5H, m), 2.15-1.60(12H, m)Purity > 90% (NMR) MS 468(M + 1) Example No. 81

1H NMR(δ) ppm 300MHz, DMSO-d6 12.75(1H, brs), 8.21(1H, d, J=1.4Hz),7.49(1H, d, J=8.6 Hz), 7.85(1H, dd, J=8.6, 1.4 Hz), 7.70-7.55(5H, m),7.23 (2H, d, J=8.7Hz), 5.25(2H, s), 4.36-4.15(1H, m), 2.39-2.18 (2H, m),2.00-1.78(4H, m), 1.70-1.57(1H, m), 1.48-1.15(3H, m) Purity > 90% (NMR)MS 495(M + 1)

[1975] TABLE 18 Example No. 82

1H NMR(δ) ppm 300MHz, DMSO-d6 8.27(1H, s), 8.22(1H, d, J=8.7 Hz),8.02(1H, d, J=8.7Hz), 7.69(2H, d, J=8.7Hz), 7.60-7.50(4H, m),7.45-7.25(8H, m), 6.75(1H, s), 4.21-4.23 (1H, m), 2.39-2.18(2H, m),2.10-1.78(4H, m), 1.70-1.15 (4H, m) Purity > 90% (NMR) MS 503(M + 1)Example No. 83

1H NMR(δ) ppm 300MHz, DMSO-d6 13.2(1H, brs), 8.30(1H, s), 8.23(1H, d,J=8.8Hz), 8.02(1H, d, J=8.7Hz), 7.74(2H, d, J=8.6Hz), 7.40-7.33(5H, m),5.22(2H, s), 4.36(1H, m), 2.50-1.40(10H, m), 1.31(18H, s). Purity > 90%(NMR) MS 539(M + 1) Example No. 84

1H NMR(δ) ppm mixture of isomers(cis:trans=3:1) 300MHz, DMSO-d6 8.30(1H,s), 8.20-7.95(2H, m), 7.72(2H, d, J=8.4Hz), 7.52-7.29(7H, m), 5.25(2H,s), 4.34, 3.40(1H, m), 2.50-2.20 (2H, m), 2.05-1.50(6H, m), 1.14,0.90(3H, d, J=6.9, 6.3 Hz), 1.09(1H, m). Purity > 90% (NMR) MS 441(M +1)

[1976] TABLE 19 Example No. 85

1H NMR(δ) ppm 300MHz, DMSO-d6 8.25(1H, s), 8.14-7.83(6H, m),7.77-7.44(5H, m), 7.21(2H, d, J=7.8Hz), 4.44(2H, brt), 4.31(1H, brt),3.56(2H, brt), 2.20-2.16(2H, m), 2.00-1.74(4H, m), 1.70-1.55(1H, m),1.45-1.14(3H, m) Purity > 90% (NMR) MS 491(M + 1) Example No. 86

1H NMR(δ) ppm 300MHz, DMSO-d6 12.75(1H, s), 8.23(1H, s), 8.15 (1H, d,J=7.6Hz), 8.02-7.53 (10H, m), 7.32(2H, d, J=8.7 Hz), 5.68(2H, s),4.32(1H, brt, J=12.2Hz), 2.41-2.20 (2H, m), 2.01-1.78(4H,m),1.71-1.56(1H, m), 1.50-1.16(3H, m) Purity > 90% (NMR) MS 477(M + 1)Example No. 87

1H NMR(δ) ppm 300MHz, DMSO-d6 12.75(1H, brs), 8.16(1H, s), 7.91 and7.82(2H, ABq, J=8.5 Hz), 7.44 and 6.86(4H, A′B′q, J=8.6Hz),7.39-7.26(10H, m), 4.82(2H, s), 4.35(1H, brt, J=12.2Hz), 2.35-2.16(2H,m), 1.97-1.75(4H, m), 1.69-1.56(1H, m), 1.45-1.16(3H, m) Purity > 90%(NMR) MS 516(M + 1)

[1977] TABLE 20 Example No. 88

1H NMR(δ) ppm 300MHz, DMSO-d6 8.31(1H, s), 8.26 and 8.06(2H, ABq,J=8.9Hz), 7.73 and 7.22 (4H, A′B′q, J=8.7Hz), 7.50-7.36(8H, m), 5.10(2H,s), 4.37(1H, brt, J=12.2Hz), 2.38-2.28(2H, m), 2.10-1.80(4H, m),1.70-1.56(1H, m), 1.50-1.20(3H, m) Purity > 90% (NMR) MS 503(M + 1)Example No. 89

1H NMR(δ) ppm Purity 91% (HPLC) MS 427(M + 1) Example No. 90

1H NMR(δ) ppm 300MHz, DMSO-d6 8.40-8.20(2H, m), 8.04(1H, d, J=8.4Hz),7.65(2H, d, J=8.4 Hz), 7.50-7.10(12H, m), 5.08 (1H, m), 4.33(1H, m),3.00 (4H, m), 2.50-1.10(10H, m). Purity > 90% (NMR) MS 531(M + 1)

[1978] TABLE 21

90% Example No. Purity (NMR) 1H NMR(δ) ppm

MS 455(M + 1) 300 MHz, DMSO-d6 8.31(1H, s), 8.27(1H, d, J=8.7 Hz),8.08-8.03(3H, m), 7.77-7.58(5H, m), 7.31(2H, d, J=8.7 Hz), 5.81(2H, s),4.40(1H, m), 2.50-1.20(10H, m).

MS 419(M + 1) 300 MHz, DMSO-d6 11.8(1H, brs), 8.07(1H, s), 7.89(1H, d,J=8.7 Hz), 7.84(1H, d, J=8.4 Hz), 7.69(2H, m), 7.48(3H, m), 4.42(2H, s),4.11(1H, m), 3.73(4H, m), 3.40(4H, m), 2.40-1.40(10H, m)

MS 531(M + 1) 300 MHz, DMSO-d6 8.32(1H, s), 8.28(1H, d, J=8.9 Hz),8.05(1H, d, J=8.7 Hz), 7.72(2H, d, J=8.7 Hz), 7.38(4H, d, J=7.2 Hz),7.31(4H, t, J=7.3 Hz), 7.21-7.17(4H, m), 4.37(1H, m), 4.26(1H, t, J=7.9Hz), 4.01(2H, t, J=6.2 Hz), 2.57(2H, m), # 2.50-2.20(2H, m),2.10-2.00(2H, m), 2.00-1.75(2H, m), 1.75-1.55(1H, m), 1.55-1.20(3H, m).

[1979] TABLE 22 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 537(M + 1) 300 MHz, DMSO-d6 8.32(1H, s), 8.27(1H, d, J=9.0 Hz),8.05(1H, d, J=8.7 Hz), 7.75-7.70(3H, m), 7.56(1H, d, J=8.4 Hz),7.55-7.35(6H, m), 7.22(2H, d, J=8.7 Hz), 5.11(2H, s), 4.36(1H, m),2.40-2.15(2H, m), 2.15-1.95(2H, m), 1.95-1.75(2H, m), 1.75-1.55(1H, m),1.55-1.20(3H, m).

MS 434(M + 1) 300 Hz, DMSO-d6 12.9(1H, brs), 8.02(1H, s), 7.82(2H, m),7.40-7.25(5H, m), 4.58(2H, s), 4.09(1H, m), 3.71(1H, m), 3.49(2H, m),3.21(2H, m), 2.35-1.30(14H, m).

MS 457(M + 1) 300 MHz, DMSO-d6 8.31(1H, d, J=1.3 Hz), 8.27(1H, d, J=8.8Hz), 8.05(1H, d, J=8.8 Hz), 7.76(2H, d, J=8.7 Hz), 7.40-7.25(4H, m),7.06-6.90(3H, m), 4.53-4.26(5H, m), 2.40-2.18(2H, m), 2.12-1.56(5H, m),1.50-1.19(3H, m)

[1980] TABLE 23 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 455(M + 1) 300 MHz, DMSO-d6 8.32(1H, d, J=1.3 Hz), 8.29(1H, d, J=8.8Hz), 8.05(1H, dd, J=8.8, 1.3 Hz), 8.42(2H, d, J=8.8 Hz), 7.37-7.16(7H,m), 4.48-4.30(1H, m), 4.12(2H, t, J=6.2 Hz), 2.83-2.70(2H, m),2.40-1.50(9H, m), 1.59-1.19(3H, m)

MS 483(M + 1) 300 MHz, DMSO-d6 8.28(1H, d, J=1.3 Hz), 8.21(1H, d, J=8.8Hz), 8.01(1H, d, J=10.1 Hz), 7.70(2H, d, J=8.7 Hz), 7.33-7.12(7H, m),4.44-4.28(1H, m), 4.10(2H, t, J=6.3 Hz), 2.62(2H, t, J=7.4 Hz),2.39-2.15(2H, m), 2.10-1.18(14H, m)

MS 418(M + 1) 300 MHz, DMSO-d6 12.93(1H, brs), 8.30(1H, d, J=1.4 Hz),8.04(1H, d, J=8.7 Hz), 7.92(1H, dd, J=8.7, 1.4 Hz), 7.59-7.34(5H, m),7.07(1H, s), 5.38(2H, s), 4.78-4.60(1H, m), 2.32-2.14(2H, m),2.03-1.28(8H, m)

[1981] TABLE 24 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 427(M + 1) 300 MHz, DMSO-d6 8.46(1H, d, J=2.1 Hz) 8.16(1H, s),8.00(1H, dd, J=8.5, 2.1 Hz), 7.87(1H, d, J=8.5 Hz), 7.68(1H, d, J=8.5Hz), 7.55-7.30(5H, m), 7.08(1H, d, J=8.5 Hz), 5.45(2H, s), 4.25-4.08(1H,m), 2.39-2.18(2H, m), 2.00-1.75(4H, m), 1.70-1.55(1H, m), 1.45-1.19(3H,m)

MS 531(M + 1) 300 MHz, DMSO-d6 8.33(1H, s), 8.31(1H, d, J=6.9 Hz),8.06(1H, d, J=8.4 Hz), 7.76 and 7.29(4H, ABq, J=8.9 Hz), 6.68(2H, s),4.37(1H, m), 4.35(2H, t, J=7.0 Hz), 3.79(6H, s), 3.63(3H, s), 3.04(2H,t, J=6.9 Hz), 2.30(2H, m), 2.04(2H, m), 1.86(2H, m), 1.65(1H, m),1.50-1.15(3H, m)

MS 455(M + 1) 300 MHz, DMSO-d6 12.88(1H, s), 8.34(1H, s), 7.86(1H, d,J=8.5 Hz), 7.73(1H, d, J=8.5 Hz), 7.63 and 7.23(4H, ABq, J=8.7 Hz),7.52-7.35(5H, m), 5.22(2H, s), 4.31(1H, m), 2.39(2H, m), 1.79(2H, m),1.53(2H, m), 1.31(2H, m), 1.11(3H, s), 0.95(3H, s)

[1982] TABLE 25 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 491(M + 1) 300 MHz, DMSO-d6 12.79(1H, brs), 8.22(2H, s),8.02-7.78(4H, m), 7.63-7.42(6H, m), 7.20-7.09(2H, m), 4.43(2H, s),4.27(1H, brt, J=12.2 Hz), 3.59(2H, s), 2.39-2.15(2H, m), 1.98-1.72(4H,m), 1.68-1.59(1H, m), 1.43-1.12(3H, m)

MS 519(M + 1) 300 MHz, DMSO-d6 12.75(1H, s), 8.23(1H, s), 7.94 and7.86(2H, ABq, J=8.6 Hz), 7.64 and 7.05(4H, A′B′q, J=8.7 Hz),7.32-7.09(9H, m), 5.13(2H, s), 4.28(1H, brt, J=12.2 Hz), 2.36-2.19(2H,m), 1.95-1.77(4H, m), 1.66-1.56(1H, m), 1.46-1.10(3H, m)

MS 519(M + 1) 300 MHz, DMSO-d6 8.23(1H, s), 7.94 and 7.87(2H, ABq, J=8.6Hz), 7.68 and 7.17(4H, A′B′q, J=8.7 Hz), 7.46-7.33(6H, m), 6.93 and6.75(2H, A″B″q, J=8.2 Hz), 6.82(1H, s), 5.13(2H, s), 4.30(1H, brt,J=12.2 Hz), 2.39- # 2.18(2H, m), 1.98-1.77(4H, m), 1.71-1.59(1H, m),1.48-1.20(3H, m)

[1983] TABLE 26 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 429(M + 1) 300 MHz, DMSO-d6 12.89(1H, brs), 9.73(1H, s), 8.24(1H, s),8.03 and 7.91(2H, ABq, J=8.7 Hz), 7.66 and 7.04(4H, A′B′q, J=8.7 Hz),7.16-7.03(3H, m), 6.89(2H, t, J=9.2 Hz), 4.33(1H, brt, J=12.2 Hz),2.40-2.18(2H, m), 2.00-1.78(4H, m), 1.70-1.58(1H, m), 1.50-1.20(3H, m)

MS 429(M + 1) 300 MHz, DMSO-d6 12.98(1H, brs), 9.82(1H, brs), 8.27(1H,s), 8.09 and 7.94(2H, ABq, J=8.7 Hz), 7.74 and 7.22(4H, A′B′q, J=8.7Hz), 7.28-7.22(1H, m), 6.67-6.54(3H, m), 4.35(1H, brt, J=12.2 Hz),2.40-2.20(2H, m), 2.05-1.80(4H, m), 1.72-1.59(1H, m), 1.50-1.21(3H, m)

MS 443(M + 1) 300 MHz, DMSO-d6 8.24(1H, s), 8.01 and 7.90(2H, ABq, J=8.7Hz), 7.65 and 7.03(4H, A′B′q, J=8.7 Hz), 7.32-7.20(3H, m), 7.08-7.03(1H,m), 4.32(1H, brt, J=12.2 Hz), 3.77(3H, s), 2.36-2.20(2H, m),2.00-1.78(4H, m), 1.71-1.59(1H, m), 1.44-1.11(3H, m)

[1984] TABLE 27 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 443(M + 1) 300 MHz, DMSO-d6 12.75(1H, s), 8.24(1H, s), 7.96 and7.87(2H, ABq, J=9.0 Hz), 7.69 and 7.19(4H, A′B′q, J=8.6 Hz), 7.37(1H, t,J=7.1 Hz), 6.84-6.70(3H, m), 4.31(1H, brt, J=12.2 Hz), 3.78(3H, s),2.39-2.20(2H, m), 1.98-1.78(4H, m), 1.76-1.60(1H, m), 1.48-1.13(3H, m)

MS 471(M + 1) 300 MHz, DMSO-d6 8.31(1H, s), 8.26 and 8.04(2H, ABq, J=8.8Hz), 7.75 and 7.71(4H, A′B′q, J=8.8 Hz), 7.32-7.03(4H, m), 4.34(1H, brt,J=12.2 Hz), 3.94(2H, t, J=6.3 Hz), 2.40-2.19(2H, m), 2.11-1.81(4H, m),1.72-1.16(6H, m), 0.71(3H, t, J=7.3 Hz)

MS 471(M + 1) 300 MHz, DMSO-d6 8.22(1H, s), 7.91 and 7.87(2H, ABq, J=8.7Hz), 7.68 and 7.18(4H, A′B′q, J=8.7 Hz), 7.35(1H, t, J=8.5 Hz), 6.80(1H,d, J=9.0 Hz), 6.72-6.68(2H, m), 4.30(1H, brt, J=12.2 Hz), 3.94(2H, t,J=6.5 Hz), 2.39-2.18(2H, m), 1.97-1.58(7H, m), 1.45-1.20(3H, m),0.97(3H, t, J=7.4 Hz)

[1985] TABLE 28 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 497(M + 1) 300 MHz, DMSO-d6 12.73(1H, s), 8.22(1H, s), 7.94 and7.85(2H, ABq, J=9.3 Hz), 7.61 and 7.01(4H, A′B′q, J=8.6 Hz),7.25-7.00(4H, m), 5.25(2H, brs), 4.55(2H, d, J=6.6 Hz), 4.29(1H, brt,J=12.2 Hz), 2.38-2.18(2H, m), 1.96-1.78(4H, m), 1.70-1.56(1H, m),1.67(3H, s), 1.60(3H, s), 1.48-1.15(3H, m)

MS 497(M + 1) 300 MHz, DMSO-d6 12.75(1H, s), 8.23(1H, s), 7.95 and7.86(2H, ABq, J=8.9 Hz), 7.69 and 7.18(4H, A′B′q, J=8.9 Hz), 7.35(1H, t,J=8.3 Hz), 6.81-6.69(3H, m), 5.41(2H, brs), 4.54(2H, d, J=6.6 Hz),4.31(1H, brt, J=12.2 Hz), 2.41-2.18(2H, m), 1.98-1.76(4H, m), 1.73(3H,s), # 1.70-1.58(1H, m), 1.68(3H, s), 1.45-1.17(3H, m)

MS 499(M + 1) 300 MHz, DMSO-d6 12.73(1H, s), 8.22(1H, s), 7.94 and7.85(2H, ABq, J=8.4 Hz), 7.60 and 6.99(4H, A′B′q, J=8.6 Hz),7.29-7.00(4H, m), 4.29(1H, brt, J=12.2 Hz), 3.99(2H, t, J=6.3 Hz),2.41-2.20(2H, m), 1.95-1.76(4H, m), 1.70-1.14(7H, m), 0.76(3H, d, J=6.6Hz)

[1986] TABLE 29 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 499(M + 1) 300 MHz, DMSO-d6 8.23(1H, s), 7.93 and 7.87(2H, ABq, J=8.6Hz), 7.69 and 7.19(4H, A′B′q, J=8.6 Hz), 7.35(1H, t, J=7.8 Hz),6.82-6.69(3H, m), 4.30(1H, brt, J=12.2 Hz), 4.00(2H, t, J=6.9 Hz),2.38-2.20(2H, m), 1.97-1.54(8H, m), 1.47-1.20(3H, m), 0.93(6H, d, J=6.6Hz)

MS 557(M + 1) 300 MHz, DMSO-d6 8.30(1H, s), 8.25(1H, d, J=8.9 Hz),8.03(1H, d, J=8.8 Hz), 7.68(2H, d, J=8.8 Hz), 7.24(2H, d, J=7.2 Hz),7.19-7.10(6H, m), 6.94(2H, t, J=7.2 Hz), 4.34(1H, m), 4.19(4H, brs),3.10(4H, brs), 2.40-2.15(2H, m), 2.10-1.95(2H, m), 1.95- # 1.75(2H, m),1.75-1.55(1H, m), 1.55-1.20(3H, m).

MS 571(M + 1) 300 MHz, DMSO-d6 12.8(1H, brs), 8.22(1H, s), 7.98(1H, d,J=8.7 Hz), 7.87(1H, d, J=8.6 Hz), 7.80(2H, d, J=8.2 Hz), 7.72-7.67(3H,m), 7.59(2H, d, 3=8.7 Hz), 7.54-7.51(2H, m), 7.42-7.41(1H, m), 7.11(2H,d, J=8.8 Hz), 5.09(2H, s), 4.27(1H, m), 2.40- # 2.15(2H, m),2.00-1.75(4H, m), 1.75-1.55(1H, m), 1.55-1.15(3H, m).

[1987] TABLE 30 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 571(M + 1) 300 MHz, DMSO-d6 13.3(1H, brs), 8.30(1H, s), 8.25(1H, d,J=8.9 Hz), 8.04(1H, d, J=8.7 Hz), 7.72(2H, d, J=8.8 Hz), 7.57(4H, d,J=8.6 Hz), 7.47(4H, d, J=8.6 Hz), 7.33(2H, d, J=8.9 Hz), 6.84(1H, s),4.33(1H, m), 2.45-2.10(2H, m), 2.10-1.95(2H, m), # 1.95-1.70(2H, m),1.70-1.55(1H, m), 1.55-1.15(3H, m).

MS 471(M + 1) 300 MHz, DMSO-d6 8.32-8.30(2H, m), 8.07-8.03(1H, m), 7.74and 6.90(4H, ABq, J=8.7 Hz), 4.37(1H, m), 4.31(2H, t, J=6.8 Hz),3.74(3H, s), 3.04(2H, t, J=6.7 Hz), 2.30(2H, m), 2.02(2H, m), 1.86(2H,m), 1.63(1H, m), 1.55-1.15(3H, m)

MS 471(M + 1) 300 MHz, DMSO-d6 8.23(1H, s), 7.99(1H, d, J=8.7 Hz),7.88(1H, d, J=8.4 Hz), 7.61 and 7.16(4H, ABq, J=8.6 Hz), 7.30-7.22(2H,m), 7.01(2H, d, J=8.1 Hz), 6.92(1H, t, J=7.5 Hz), 4.28(1H, m), 4.25(2H,t, J=7.2 Hz), 3.83(3H, s), 3.07(2H, t, J=7.1 Hz), 2.28(2H, m),2.00-1.75(4H, m), # 1.70-1.55(1H, m), 1.50-1.15(3H, m)

[1988] TABLE 31 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 471(M + 1) 300 MHz, DMSO-d6 12.85(1H, brs), 8.24(1H, s), 8.01(1H, d,J=8.7 Hz), 7.90(1H, d, J=8.6 Hz), 7.62 and, 7.17(4H, ABq, J=8.7 Hz),7.24(1H, m), 6.94(2H, m), 6.82(1H, m), 4.32(2H, t, J=6.7 Hz), 3.76(3H,s), 3.07(2H, t, J=6.7 Hz), 2.29(2H, m), 2.00-1.75(4H, m), 1.70- #1.55(1H, m), 1.50-1.15(3H, m)

MS 441(M + 1) 300M Hz, DMSO-d6 12.8(1H, brs), 8.22(1H, s), 7.87(2H, m),7.62(2H, d, J=8.1 Hz), 7.60-7.20(7H, m), 5.23(2H, s), 4.46(1H, m),2.50-2.30(2H, m), 1.70-1.40(10H, m).

MS 553(M + 1) 300 MHz, DMSO-d6 8.24(1H, s), 7.97(1H, d, J=9.0 Hz),7.87(1H, d, J=8.4 Hz), 7.65(2H, d, J=8.7 Hz), 7.40-7.05(9H, m), 7.03(2H,d, J=8.4 Hz), 4.31(1H, m), 4.18(2H, t, J=6.6 Hz), 2.81(2H, t, J=6.3 Hz),2.40-2.20(2H, m), 2.00-1.70(4H, m), 1.70- # 1.50(1H, m), 1.50-1.05(3H,m).

[1989] TABLE 32 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 533(M + 1) 300 MHz, DMSO-d6 13.1(1H, brs), 8.29(1H, s), 8.17(1H, d,J=8.7 Hz), 7.99(1H, d, J=8.7 Hz), 7.77(2H, d, J=8.7 Hz), 7.40-7.20(8H,m), 6.84(1H, d, J=9.3 Hz), 6.75-6.72(2H, m), 4.36(1H, m), 4.22(2H, t,J=6.8 Hz), 3.04(2H, t, J=6.7 Hz), 2.40-2.15(2H, m), 2.15- # 1.95(2H, m),1.95-1.75(2H, m), 1.75-1.55(1H, m), 1.55-1.15(3H, m).

MS 517(M + 1) 300 MHz, DMSO-d6 8.32(1H, s), 8.28(1H, d, J=8.7 Hz),8.05(1H, d, J=9.0 Hz), 7.73(2H, d, J=9.0 Hz), 7.43(4H, d, J=7.2 Hz),7.36-7.20(8H, m), 4.74(2H, d, J=7.5 Hz), 4.57(1H, t, J=7.5 Hz), 4.38(1H,m), 2.40-2.15(2H, m), 2.15-1.95(2H, m), 1.95- # 1.85(2H, m),1.85-1.55(1H, m), 1.55-1.20(3H, m).

MS 425(M + 1) 300 MHz, DMSO-d6 8.32(1H, s), 8.14(1H, d, J=8.7 Hz),8.03(1H, d, J=8.7 Hz), 7.77(2H, d, J=9.0 Hz), 7.52-7.31(7H, m), 5.74(2H,m), 5.26(2H, s), 4.61(1H, m), 2.96(1H, m), 2.60-2.10(5H, m).

[1990] TABLE 33 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 445(M + 1) 300 MHz, DMSO-d6 13.2(1H, brs), 8.33(1H, s), 8.12(1H, d,J=8.7 Hz), 7.96(1H, d, J=8.8 Hz), 7.79(2H, d, J=8.7 Hz), 7.52-7.32(7H,m), 5.26(2H, s), 4.92(1H, d, J=49.4 Hz), 4.57(1H, m), 2.65-2.35(2H, m),2.25-1.50(6H, m).

MS 505(M + 1) 300 MHz, DMSO-d6 8.21(1H, s), 7.92 and 7.85(2H, ABq, J=8.6Hz), 7.61 and 7.06(4H, A′B′q, J=8.6 Hz), 7.36-6.91(9H, m), 4.24(1H, brt,J=12.2 Hz), 2.35-2.15(2H, m), 1.95-1.75(4H, m), 1.70-1.58(1H, m),1.48-1.14(3H, m)

MS 505(M + 1) 300 MHz, DMSO-d6 8.21(1H, s), 7.92 and 7.86(2H, ABq, J=8.6Hz), 7.69 and 7.22(4H, A′B′q, J=8.6 Hz), 7.52-7.39(1H, m), 7.47 and7.41(2H, A″B″q, J=8.1 Hz), 6.91(1H, d, J=8.0 Hz), 6.89(1H, d, J=8.2 Hz),6.75(1H, s), 4.36-4.18(1H, m), # 2.38-2.17(2H, m), 1.95-1.76(4H, m),1.70-1.59(1H, m), 1.44-1.19(3H, m)

[1991] TABLE 34 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 590(M + 1) 300 MHz, DMSO-d6 8.27(1H, s), 7.69(2H, d, J=8.6 Hz),7.49-7.21(11H, m), 5.08 and 5.03(2H, ABq, J=12.6 Hz), 5.07-4.99(1H, m),4.26(2H, d, J=6.6 Hz), 2.40-2.18(2H, m), 2.04-1.77(4H, m), 1.70-1.58(1H,m), 1.48-1.15(3H, m)

MS 589(M + 1) 300 MHz, DMSO-d6 8.29(1H, s), 8.11(1H, d, J=9.0 Hz),7.96(1H, d, J=8.4 Hz), 7.80(2H, d, J=8.1 Hz), 7.72-7.41(7H, m), 7.12(1H,d, J=12.6 Hz), 7.01(1H, d, J=8.4 Hz), 5.12(2H, s), 4.06(1H, m),2.35-2.10(2H, m), 2.00-1.75(4H, m), 1.75-1.55(1H, m), 1.60-1.20(3H, m).

MS 519(M + 1) 300 MHz, DMSO-d6 12.8(1H, brs), 8.23(1H, s), 7.97(1H, d,J=8.7 Hz), 7.87(1H, d, J=8.6 Hz), 7.66(2H, d, J=8.6 Hz), 7.49-7.33(5H,m), 7.17-7.05(6H, m), 5.12(2H, s), 4.31(1H, m), 2.40-2.15(2H, m),2.05-1.20(8H, m).

[1992] TABLE 35 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 531(M + 1) 300 MHz, DMSO-d6 8.57(1H, s), 8.01(1H, d, J=8.7 Hz),7.66(1H, d, J=8.7 Hz), 7.51(2H, d, J=8.7 Hz), 7.31(4H, d, J=8.0 Hz),7.16(4H, d, J=8.0 Hz), 7.09(2H, d, J=8.7 Hz), 6.26(1H, s), 4.37(1H, m),2.41-2.28(2H, m), 2.33(6H, s), 2.03-1.84(4H, m), 1.77(1H, m),1.45-1.20(3H, m).

MS 539(M + 1) 8.59(1H, d, J=1.5 Hz), 8.02(1H, dd, J=8.7, 1.5 Hz),7.68(1H, d, J=8.7 Hz), 7.54(2H, d, J=8.8 Hz), 7.39(4H, dd, J=8.7, 5.3Hz), 7.08(4H, d, J=8.7 Hz), 7.05(2H, d, J=8.8 Hz), 6.29(1H, s), 4.36(1H,m), 2.43-2.19(2H, m), 2.04-1.85(4H, m), 1.78(1H, m), 1.45-1.23(3H, m).

MS 485(M + 1) 300 MHz, DMSO-d6 12.34(1H, brs), 7.93(1H, s), 7.55(1H, d,J=8.6 Hz), 7.33-7.15(6H, m), 7.11(2H, d, J=8.6 Hz), 4.30-4.20(1H, m),4.07(2H, t, J=6.3 Hz), 3.93(3H, s), 2.78(2H, t, J=7.4 Hz), 2.35-2.19(2H,m), 2.12-2.00(2H, m), 1.91-1.79(4H, m), 1.69-1.60(1H, m), 1.47-1.20(3H,m)

[1993] TABLE 36 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 471(M + 1) 300 MHz, DMSO-d6 8.13(1H, s), 7.65(2H, d, J=8.7 Hz),7.63(1H, s), 7.35-7.12(7H, m), 4.35-4.20(1H, m), 4.10(1H, t, J=6.3 Hz),2.78(2H, t, J=7.5 Hz), 2.33-1.78(8H, m), 1.70-1.16(4H, m)

MS 469(M + 1) 300 MHz, DMSO-d6 8.24(1H, s), 8.11(1H, s), 7.76(2H, d,J=9.0 Hz), 7.37-7.16(7H, m), 4.43-4.30(1H, m), 4.13(2H, t, J=6.3 Hz),2.84-2.68(5H, m), 2.42-2.22(2H, m), 2.18-1.80(6H, m), 1.70-1.20(4H, m)

MS 547(M + 1) 300 MHz, DMSO-d6 12.73(1H, brs), 8.22(1H, s), 7.76(1H, d,J=8.7 Hz), 7.85(1H, d, J=8.7 Hz), 7.54-7.49(4H, m), 7.42-7.21(5H, m),7.11-7.09(3H, m), 6.93(1H, m), 5.17(2H, s), 4.29(3H, m), 3.11(2H, m),2.40-2.20(2H, m), 1.99-1.23(8H, m)

[1994] TABLE 37 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 547(M + 1) 300 MHz, DMSO-d6 12.73(1H, brs), 8.22(1H, s), 7.93(1H, d,J=8.7 Hz), 7.73(1H, m), 7.60-7.57(2H, m), 7.47-6.90(1H, m), 5.11(2H, s),4.33-4.28(3H, m), 3.09-3.04(2H, t, J=6.7 Hz), 2.35-2.20(2H, m),1.95-1.10(8H, m)

MS 487(M + 1) 300 MHz, DMSO-d6 12.83(2H, brs), 8.22(1H, s), 7.94(1H, d,J=8.7 Hz), 7.85(1H, d, J=8.4 Hz), 7.63-7.60(2H, m), 7.26-7.03(6H, m),4.73(2H, s), 4.30(1H, m), 2.40-2.15(2H, m), 2.00-1.20(8H, m)

MS 487(M + 1) 300 MHz, DMSO-d6 12.87(1H, brs), 8.24(1H, s), 7.97(1H, d,J=9.0 Hz), 7.87(1H, d, J=8.7 Hz), 7.69 and 7.19 (4H, ABq, J=8.7 Hz),7.36(1H, t, J=8.7 Hz), 6.80-6.72(3H, m), 4.71(2H, s), 4.32(1H, m),2.29(2H, m), 1.95-1.25(8H, m)

[1995] TABLE 38 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 551(M + 1) 300 MHz, DMSO-d6 8.32(1H, s), 8.27(1H, d, J=8.7 Hz),8.05(1H, d, J=9.0 Hz), 7.76-7.72(3H, m), 7.54(1H, d, J=8.4 Hz),7.39-7.22(7H, m), 5.11(1H, s), 4.36(1H, m), 2.35(3H, s), 2.35-2.15(2H,m), 2.15-1.95(2H, m), 1.95-1.75(2H, m), 1.75-1.55(1H, m), 1.55-1.15(3H,m).

MS 567(M + 1) 300 MHz, DMSO-d6 13.1(1H, brs), 8.30(1H, s), 8.24(1H, d,J=8.8 Hz), 8.03(1H, d, J=8.7 Hz), 7.74-7.71(3H, m), 7.52(1H, d, J=8.3Hz), 7.40-7.36(3H, m), 7.23(2H, d, J=8.8 Hz), 7.01(2H, d, J=8.7 Hz),5.11(2H, s), 4.35(1H, m), 3.79(3H, s), 2.45-2.15(2H, m), 2.15-1.95(2H,m), 1.95-1.75(2H, m), 1.75-1.55(1H, m), 1.55-1.15(3H, m).

MS 585(M + 1) 300 MHz, DMSO-d6 13.0(1H, brs), 8.31(1H, s), 8.23(1H, d,J=8.7 Hz), 8.04(1H, d, J=8.7 Hz), 7.80(2H, d, J=8.3 Hz), 7.70-7.66(3H,m), 7.55-7.40(4H, m), 7.03-6.95(2H, m), 5.08(2H, s), 4.03(1H, m),2.40-2.15(2H, m), 2.18(3H, s), 2.05-1.70(4H, m), 1.70-1.50(1H, m),1.50-1.10(3H, m).

[1996] TABLE 39 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 593(M + 1) 300 MHz, DMSO-d6 8.31(1H, s), 8.23(1H, d, J=8.8 Hz),8.02(1H, d, J=8.7 Hz), 7.73-7.71(3H, m), 7.54(1H, d, J=8.3 Hz), 7.48(2H,d, J=8.4 Hz), 7.41-7.37(3H, m), 7.22(2H, d, J=8.7 Hz), 5.13(2H, s),4.34(1H, m), 2.40-2.20(2H, m), 2.15-1.95(2H, m), 1.95-1.75(2H, m),1.70-1.55(1H, m), 1.50-1.15(3H, m), 1.31(9H, s).

MS 555(M + 1) 300 MHz, DMSO-d6 8.29(1H, s), 8.13(1H, d, J=8.7 Hz),7.97(1H, d, J=8.6 Hz), 7.76(1H, d, J=2.1 Hz), 7.63(1H, t, J=8.5 Hz),7.57(1H, dd, J=8.2, 2.2 Hz), 7.55-7.35(6H, m), 7.15(1H, d, J=12.1 Hz),7.02(1H, d, J=8.6 Hz), 5.10(2H, s), 4.07(1H, m), 2.35-2.10(2H, m),2.00-1.70(4H, m), 1.70-1.55(1H, m), 1.50-1.15(3H, m).

MS 605(M + 1) 300 MHz, CDCl3 8.61(1H, s), 8.04(1H, d, J=8.7 Hz),7.69(1H, d, J=8.7 Hz), 7.66(1H, d, J=2.4 Hz), 7.59(2H, d, J=8.7 Hz),7.42(1H, dd, J=8.0, 2.4 Hz), 7.38(1H, t, J=1.8 Hz), 7.28(2H, d, J=1.8Hz), 7.26(1H, d, J=8.0 Hz), 7.03(2H, d, J=8.7 Hz), 4.94(2H, s), 4.37(1H,m), 2.43-2.21(2H, m), 2.17-1.86(4H, m), # 1.79(1H, m), 1.43-1.26(3H, m).

[1997] TABLE 40 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 557(M + 1) 300 MHz, DMSO-d6 8.21(s, 1H), 7.89(1H, d, J=8.7 Hz),7.87(1H, d, J=8.7 Hz), 7.63-7.46(5H, m), 7.30-7.12(5H, m), 7.08(1H, d,J=11.0 Hz), 6.81(1H, s), 3.92(1H, m), 2.15-2.06(2H, m), 1.89-172(4H, m),1.61(1H, m), 1.42-1.09(3H, m).

MS 553(M + 1) 300 MHz, DMSO-d6 8.24(1H, d, J=1.5 Hz), 7.96(1H, d, J=9.0Hz), 7.88(1H, dd, J=9.0, 1.5 Hz), 7.58(1H, d, J=8.7 Hz), 7.50-7.30(5H,m), 7.22-7.00(6H, m), 5.13(2H, s), 3.98-3.80(1H, s), 2.36-1.10(10H, m)

MS 587(M + 1) 300 MHz, DMSO-d6 8.23(1H, s), 8.95(1H, d, J=8.4 Hz),7.88(1H, d, J=8.7 Hz), 7.66(1H, d, J=8.4 Hz), 7.52-7.28(7H, m), 7.23(2H,d, J=9.3 Hz), 7.14(2H, d, J=8.7 Hz), 5.14(2H, s), 3.90-3.72(1H, m),2.20-1.10(10H, m)

[1998] TABLE 41 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 605(M + 1) 300 MHz, DMSO-d6 8.18(1H, s), 7.92-7.78(3H, m),7.78-7.58(3H, m), 7.58-7.44(4H, m), 7.29(1H, d, J=8.2Hz), 7.01(2H, d,J=8.7 Hz), 4.88(1H, d, J=11.8 Hz), 4.80(1H, d, J=11.8 Hz), 4.22(1H, m),2.37-2.16(2H, m), 1.95-1.75(4H, m), 1.64(1H, m), 1.48-1.14(3H, m).

MS 456(M + 1) 300 MHz, DMSO-d6 8.21(2H, m), 7.99-7.80(2H, m),7.63-7.08(9H, m), 4.20-3.98(4H, m), 2.20-2.15(2H, m), 1.95-1.74(4H, m),1.70-1.54(1H, m), 1.44-1.14(3H, m)

MS 489(M + 1) 300 MHz, DMSO-d6 8.20(1H, s), 8.93 and 7.83(2H, ABq, J=8.7Hz), 7.86-7.21(1H, m), 7.03(2H, d, J=8.7 Hz), 4.20(1H, brt, J=12.2 Hz),2.32-2.13(2H, m), 1.92-1.74(4H, m), 1.69-1.58(1H, m), 1.45-1.15(3H, m)

[1999] TABLE 42 >90% Example No. Purity (NMR) 1H NMR(δ) ppm

MS 489(M + 1) 300 MHz, DMSO-d6 8.23(1H, s), 7.94 and 7.86(2H, ABq, J=8.6Hz), 7.72-7.16(13H, m), 5.25(2H, brs), 4.55(2H, d, J=6.6 Hz), 4.31(1H,brt, J=12.2 Hz), 2.37-2.18(2H, m), 1.98-1.77 (4H, m), 1.70-1.58(1H, m),1.48-1.20 (3H, m)

MS 626(M + 1) 300 MHz, DMSO-d6 8.21(1H, s), 7.85 and 7.61(2H, ABq, J=8.7Hz), 7.61 and 6.99(4H, A′B′q, J=8.7 Hz), 7.28-7.18(1H, m), 7.25(2H, d,J=7.5 Hz), 7.07-6.99(1H, m), 4.30(1H, brt, J=12.2 Hz), 3.83 (2H, d,J=6.0 Hz), # 3.82-3.72(1H, m), 2.68-2.49(2H, m), 2.39-2.21 (2H, m),1.95-1.80(4H, m), 1.79-1.60(2H, m), 1.46-1.22 (5H, m), 1.30 (9H, s),1.00-0.82(2H, m)

MS 626(M + 1) 300 MHz, DMSO-d6 8.22(1H, s), 7.92 and 7.86(2H, ABq, J=8.7Hz), 7.68 and 7.18(4H, A′B′q, J=8.7 Hz), 7.35 (1H, t, J=8.5 Hz),6.80(1H, d, J=8.3 Hz), 6.72-6.70(2H, m), 4.30 (1H, brt, J=12.2 Hz),3.99(2H, brd, J=12.0 Hz), 3.85(2H, # d, J=6.3 Hz), 2.82-2.62(2H, m),2.38-2.20(2H, m), 1.99-1.59 (8H, m), 1.42-1.03(5H, m), 1.39 (9H, s)

[2000] TABLE 43 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 627(M + 1) 300 MHz, DMSO-d6 12.78(1H, brs), 8.22(1H, s), 7.96(1H, d,J=8.6 Hz), 7.86(1H, d, J=8.6 Hz), 7.75(1H, d, J=2.2 Hz), 7.60(2H, d,J=8.4 Hz), 7.55(1H, dd, J=8.3, 2.2 Hz), 7.48(1H, d, J=8.3 Hz), 7.18(2H,d, J=8.4 Hz), 6.73(2H, s), 5.08(2H, s), 4.23(1H, m), 3.68(9H, s), #2.37-2.17(2H, m), 1.99-1.79(4H, m), 1.65(1H, s), 1.49-1.15(3H, m).

MS 517(M + 1) 300 MHz, DMSO-d6 12.75(1H, brs), 8.22(1H, s), 7.93(2H, d,J=8.7 Hz), 7.85(2H, d, J=8.5 Hz), 7.53-7.21(10H, m), 6.94(2H, d, J=8.7Hz), 4.30-4.12(3H, m), 3.05(2H, m), 2.35-2.15(2H, m), 1.95-1.75(4H, m),1.75-1.55(1H, m), 1.50-1.10(3H, m)

MS 503(M + 1) 300 MHz, DMSO-d6 12.77(1H, brs), 8.22(1H, s), 7.95(1H, d,8.6 Hz), 7.86(1H, d, 8.6 Hz), 7.80(1H, s), 7.70-7.35(10H, m), 7.27(2H,d, J=8.7 Hz), 5.30(2H, s), 4.28(1H, m), 2.35-2.15(2H, m), 1.95-1.75(4H,m), 1.70-1.55(1H, m), 1.50-1.15(3H, m)

[2001] TABLE 44 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 526(M + 1) 300 MHz, DMSO-d6 8.90(1H, brs), 8.59(1H, brs), 8.33(1H,s), 8.18 and 8.00 (2H, ABq, J=8.5 Hz), 7.73 and 7.10(4H, A′B′q, J=8.5Hz), 7.32-7.05(4H, m), 4.35(1H, brt, J=12.2 Hz), 3.86(2H, d, J=6.3 Hz),3.25-3.08(2H, m), 2.85-2.66(2H, m), 2.40-2.28(2H, m), 2.07-1.14(15H, m)

MS 526(M + 1) 300 MHz, DMSO-d6 9.05(1H, brs), 8.76(1H, brs), 8.31(1H,s), 8.19 and 8.00 (2H, ABq, J=8.3 Hz), 7.79 and 7.25(4H, A′B′q, J=8.3Hz), 7.39(1H, brs), 6.86-6.74(4H ,m), 4.37(1H, brt, J=12.2 Hz), 3.89(2H,d, J=5.0 Hz), 3.35-3.18(2H, m), 2.98-2.75(2H, m), 2.38- # 2.17(2H, m),2.16-1.15(15H, m)

MS 498(M + 1) 300 MHz, DMSO-d6 12.87(1H, brs), 8.58(1H, d, J=6.0 Hz),8.23(1H, s), 7.99 and 7.80(2H, ABq, J=8.6 Hz), 7.61 and 7.18(4H, A′B′q,J=8.0 Hz), 7.45-7.30(5H, m), 5.29(1H, brs), 4.26(1H, brt, J=12.2 Hz),2.37-2.11(2H, m), 2.00-1.71(4H, m), 1.92(3H s), # 1.70-1.52(1H, m),1.45-1.11(3H, m)

[2002] TABLE 45 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 511(M + 1) 300 MHz, DMSO-d6 8.23(1H, s), 7.95 and 7.86(2H, ABq, J=8.6Hz), 7.69 and 7.18(4H, A′B′q, J=8.6 Hz), 7.35(1H, t, J=8.6 Hz), 6.80(1H,d, J=7.5 Hz), 6.72-6.69(2H, m), 5.20(1H, t, J=3.7 Hz), 4.31(1H, brt,J=12.2 Hz), 3.95(2H, t, J=6.8 Hz), 2.49-2.19(4H, m), 1.97- # 1.76(4H,m), 1.68(3H, s), 1.67-1.54(1H, m), 1.61(3H, s), 1.45-1.20(3H, m)

MS 497(M + 1) 300 MHz, DMSO-d6 8.20(1H, s), 7.87(2H, s), 7.68 and7.18(4H, ABq, J=8.7 Hz), 7.35(1H, t, J=7.9 Hz), 6.81(1H, d, J=9.4 Hz),6.72(1H, s), 6.71(1H, d, J=6.8 Hz), 4.80(2H, s), 4.29(1H, brt, J=12.2Hz), 4.10(1H, t, J=6.7 Hz), 2.43(1H, t, J=6.7 Hz), 2.39-2.19(2H, m),1.97- # 1.78(4H, m), 1.76(3H, s), 1.70-1.56(1H, m), 1.43-1.19(3H, m)

MS 300 MHz, DMSO-d6 11.21(1H, brs), 8.33(1H, s), 8.25(1H, d, J=8.6 Hz),8.04(1H, d, J=8.6 Hz), 7.78(2H, d, J=8.7 Hz), 7.70-7.67(2H, m),7.55-7.42(3H, m), 7.27(2H, d, J=8.7 Hz), 4.73-4.30(5H, m), 4.20-3.97(1H,m), 3.42-3.10(2H, m), 2.45-1.23(14H, m)

[2003] TABLE 46 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 583(M + 1) 300 MHz, DMSO-d6 8.27(1H, s), 8.13(1H, d, J=8.4 Hz),7.97(1H, d, J=9.0 Hz), 7.73(1H, d, J=1.8 Hz), 7.68(2H, d, J=8.4 Hz),7.54(1H, dd, J=8.4, 2.1 Hz), 7.41-7.31(5H, m), 7.19(2H, d, J=8.4 Hz),5.10(2H, s), 4.32(1H, m), 2.50(3H, s), 2.40-2.15(2H, m), 2.10-1.75(4H,m), 1.75-1.55(1H, m), 1.55-1.10(3H, m).

MS 615(M + 1) 300 MHz, DMSO-d6 8.25(1H, s), 8.09(1H, d, J=8.4 Hz),8.00(2H, d, J=8.4 Hz), 7.94(1H, d, J=8.7 Hz), 7.80(1H, d, J=2.1 Hz),7.73(2H, d, J=8.1 Hz), 7.65(2H, d, J=8.7 Hz), 7.60(1H, dd, J=8.1, 2.1Hz), 7.44(1H, d, J=8.1 Hz), 7.16(2H, d, J=8.7 Hz), 5.13(2H, s), 4.30(1H,m), 3.26(3H, s), # 2.40-1.15(2H, m), 2.05-1.75(4H, m), 1.75-1.55(1H, m),1.55-1.15(3H, m).

MS 543(M + 1) 300 MHz, DMSO-d6 13.1(1H, brs), 8.32(1H, s), 8.28(1H, d,J=8.8 Hz), 8.05(1H, d, J=8.7 Hz), 7.80-7.75(3H, m), 7.69(1H, d, J=4.1Hz), 7.57(2H, m), 7.34-7.29(3H, m), 7.20-7.15(1H, m), 5.24(2H, s),4.39(1H, m), 2.45-2.20(2H, m), 2.20-1.95(2H, m), 1.95-1.75(2H, m),1.75-1.55(1H, m), 1.55-1.15(3H, m).

[2004] TABLE 47 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 571(M + 1) 300 MHz, DMSO-d6 8.31(1H, s), 8.26(1H, d, J=8.7 Hz),8.05(1H, d, J=8.7 Hz), 7.78-7.71(3H, m), 7.59-7.41(6H, m), 7.23(2H, d,J=9.0 Hz), 5.11(2H, s), 4.35(1H, m), 2.40-2.15(2H, m), 2.15-1.95(2H, m),1.95-1.75(2H, m), 1.75-1.55(1H, m), 1.55-1.15(3H, m).

MS 538(M + 1) 300 MHz, DMSO-d6 12.7(1H, brs), 8.66(1H, s), 8.61(1H, m),8.21(1H, s), 7.92-7.79(4H, m), 7.61-7.56(3H, m), 7.50-7.43(2H, m),7.10(2H, d, J=8.7 Hz), 5.09(2H, s), 4.26(1H, m), 2.40-2.15(2H, m),2.00-1.75(4H, m), 1.75-1.55(1H, m), 1.50-1.15(3H, m).

MS 555(M + 1) 300 MHz, DMSO-d6 8.31(1H, s), 8.25(1H, d, J=8.7 Hz),8.04(1H, d, J=8.7 Hz), 7.74-7.71(3H, m), 7.57-7.46(3H, m), 7.39(1H, d,J=8.1 Hz), 7.31-7.21(4H, m), 5.11(2H, s), 4.35(1H, m), 2.40-2.15(2H, m),2.15-1.95(2H, m), 1.95-1.75(2H, m), 1.75-1.55(1H, m), 1.55-1.15(3H, m).

[2005] TABLE 48 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 537(M + 1) 300 MHz, DMSO-d6 8.24(1H, s), 7.99(1H, d, J=8.7 Hz),7.88(1H, d, J=10.5 Hz), 7.70(1H, dd, J=11.4, 1.8 Hz), 7.48-7.32(6H, m),7.17-7.09(5H, m), 5.12(2H, s), 4.30(1H, m), 2.40-2.15(2H, m),2.05-1.75(4H, m), 1.75-1.55(1H, m), 1.55-1.20(3H, m).

MS 540(M + 1) 300 MHz, DMSO-d6 8.33(1H, s), 8.29(1H, d, J=8.7 Hz),8.06(1H, d, J=8.7 Hz), 7.82-7.74(4H, m), 7.45(1H, dd, J=8.4, 3.0 Hz),7.39(2H, d, J=8.7 Hz), 5.28(2H, s), 4.40(1H, m), 2.40-2.15(2H, m),2.15-1.95(2H, m), 1.95-1.75(2H, m), 1.75-1.55(1H, m), 1.55-1.15(3H, m).

MS 590(M + 1) 300 MHz, DMSO-d6 12.80(1H, brs), 8.26(1H, s), 8.01(1H, d,J=8.7 Hz), 7.85(1H, d, J=8.7 Hz), 7.80-7.70(1H, m), 7.60-7.36(7H, m),7.18-6.91(2H, m), 5.09(2H, s), 4.11-3.90(1H, m), 2.32-1.18(14H, m)

[2006] TABLE 49 >90% Example No. Purity (NMR) 1H NMR(δ) ppm

MS 568(M + 1) 300 MHz, DMSO-d6 12.75(1H, s), 8.21(1H, s), 7.94 and7.85(2H, ABq, J=8.7 Hz), 7.61 and 7.00(4H, A′B′q, J=8.5 Hz),7.31-6.91(2H, m), 7.25(2H, d, J=7.7 Hz), 5.41(2H, brs), 4.54(2H, d,J=6.6 Hz), 4.35-4.14(2H, m), 2.49-2.15(3H, m), 1.95-1.55(5H, m), #1.50-1.13(5H, m), 1.10-0.77(2H, m)

MS 568(M + 1) 300 MHz, DMSO-d6 8.24(1H, s), 7.97 and 7.87(2H, ABq, J=8.6Hz), 7.69 and 7.19 (4H, A′B′q, J=8.6 Hz), 7.35(1H, t, J=8.1 Hz),6.81(1H, d, J=9.2 Hz), 6.72(1H, s), 6.71(1H, d, J=6.5 Hz), 4.48-4.20(2H,m), 3.95-3.75(3H, m), 3.03(1H, t, J=12.3 Hz), 2.60-2.40(1H, m), #2.39-2.15(2H, m), 2.07-1.58 (6H, m), 1.99(3H, s), 1.50-1.00(5H, m)

MS 467(M + 1) 300 MHz, DMSO-d6 12.76(1H, s), 8.23(1H, s), 7.96 and7.86(2H, ABq, J=8.6 Hz), 7.69 and 7.20 (4H, A′B′q, J=8.6 Hz), 7.39(1H,t, J=8.2 Hz), 6.86(1H, d, J=8.3 Hz), 6.81(1H, s), 6.76(1H, d, J=8.0 Hz),4.83(2H, s), 4.31(1H, brt, J=12.2 Hz), 2.39-2.19(2H, m), 1.99-1.79(4H,m), # 1.70-1.58 (1H, m), 1.48-1.20(3H, m)

[2007] TABLE 50 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 520(M + 1) 300 MHz, DMSO-d6 12.85(1H, s), 8.75(1H, s), 8.63(2H, d,J=3.8 Hz), 8.25(1H, s), 8.04-8.01(2H, m), 8.02 and 7.90(2H, ABq, J=8.6Hz), 7.72 and 7.20 (4H, A′B′q, J=8.6 Hz), 7.57(2H, dd, J=7.8, 5.0 Hz),7.40(1H, t, J=8.2 Hz), 6.93(1H, d, J=8.2 Hz), 6.87(1H, s), # 6.77(1H, d,J=8.2 Hz), 5.23(2H, s), 4.33(1H, brt, J=12.2 Hz), 2.40-2.18(2H, m),2.00-1.55(5H, m), 1.50-1.15(3H, m)

MS 457(M + 1) 300 MHz, DMSO-d6 8.32(1H, s), 8.29(1H, d, J=9.0 Hz),8.06(1H, d, J=8.7 Hz), 7.61(1H, d, J=8.4 Hz), 7.58-7.32(5H, m), 6.98(1H,d, J=2.1 Hz), 6.93(1H, dd, J=8.7, 2.1 Hz), 5.27(2H, s), 4.16-4.00(1H,m), 3.87(3H, s), 2.20-2.12(2H, m), 2.02-1.98(4H, m), 1.70- # 1.60(1H,m), 1.52-1.10(3H, m)

MS 536(M + 1) 300 MHz, DMSO-d6 8.21(1H, s), 7.91(1H, d, J=8.6 Hz),7.85(1H, d, J=8.6 Hz), 7.63(2H, d, J=8.4 Hz), 7.60(1H, d, J=9.0 Hz),7.25(2H, d, J=8.4 Hz), 7.23(1H, d, J=3.0 Hz), 6.95(1H, dd, J=9.0, 3.0Hz), 5.19(2H, s), 4.30(1H, m), 3.78(3H, s), 2.40-2.19(2H, m), 2.00- #1.87(4H, m), 1.66(1H, m), 1.49-1.18(3H, m).

[2008] TABLE 51 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 547(M + 1) 300 MHz, DMSO-d6 8.19(1H, s), 7.95(1H, d, J=8.7 Hz),7.86(1H, d, J=8.7 Hz), 7.65(4H, d, J=7.4 Hz), 7.47(2H, d, J=8.7 Hz),7.44-7.27(6H, m), 6.99(2H, d, J=8.7 Hz), 4.20(1H, m), 2.34-2.12(2H, m),1.98-1.75(4H, m), 1.64(1H, m), 1.46-1.13(3H, m).

MS 582(M + 1) 300 MHz, DMSO-d6 8.55(1H, d, J=2.1 Hz), 8.32(1H, m),8.21(1H, s), 7.95(1H, d, J=8.4 Hz), 7.86(1H, d, J=7.8 Hz), 7.68-7.56(7H,m), 7.14(2H, d, J=8.7 Hz), 5.21(1H, s), 4.26(1H, m), 2.35-2.15(2H, m),2.00-1.75(4H, m), 1.74-1.55(1H, m), 1.50-1.15(3H, m)

MS 594(M + 1) 300 MHz, DMSO-d6 10.16(1H, s), 8.25(1H, s), 8.07(1H, d,J=8.7 Hz), 7.94-7.87(2H, m), 7.71-7.62(3H, m), 7.50-7.42(4H, m),7.30(1H, d, J=8.4 Hz), 7.14(2H, d, J=8.4 Hz), 5.06(2H, s), 4.31(1H, m),2.35-2.15(2H, m), 2.05-1.75(4H, m), 1.75-1.55(1H, m), 1.50-1.15(3H, m)

[2009] TABLE 52 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 581(M + 1) 300 MHz, DMSO-d6 13.2(2H, brs), 8.30(1H, s), 8.26(1H, d,J=8.8 Hz), 8.04(1H, d, J=8.8 Hz), 8.00(2H, d, J=8.2 Hz), 7.79(1H, s),7.73 (2H, d, J=8.7 Hz), 7.61-7.56(3H, m), 7.44(1H, d, J=8.3 Hz),7.23(2H, d, J=8.8 Hz), 5.13(2H, s), 4.35(1H, m), 2.45-2.15(2H, m), 2.15-# 1.95(2H, m), 1.95-1.75(1H, m), 1.75-1.15(3H, m).

MS 554(M + 1) 300 MHz, DMSO-d6 8.30(1H, m), 8.24(1H, d, J=9.0 Hz),8.03(1H, d, J=9.0 Hz), 7.79-7.10(9H, m), 5.20-5.07(2H, m), 4.43-4.04(4H,m), 3.50-3.36(2H, m), 2.40-1.19(14H, m)

MS 605(M + 1) (DMSO-d6) δ: 8.29(1H, brs), 8.10(1H, d, J=8.4 Hz),7.97(1H, d, J=8.4 Hz), 7.79(2H, d, J=8.4 Hz), 7.74-7.67(1H, m), 7.68(2H,d, J=8.4 Hz), 7.61(1H, d, J=8.4 Hz), 7.57-7.50(2H, m), 7.46-7.39(1H, m),7.29(1H, d, J=2.4 Hz), 7.11(1H, dd, J=2.4, 8.4 Hz), 5.12(2H, s), #3.99-3.84(1H, m), 2.35-1.72(6H, m), 1.68-1.55(1H, m), 1.42-1.10(3H, m)

[2010] TABLE 53 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 520(M + 1) 300 MHz, DMSO-d6 12.76(1H, s), 8.57(1H, d, J=4.4 Hz),8.23(1H, s), 7.96 and 7.86(2H, ABq, J=8.2 Hz), 7.87-7.82(1H, m), 7.68and 7.12(4H, A′B′q, J=8.6 Hz), 7.53(2H, d, J=7.8 Hz), 7.37(1H, t, J=8.3Hz), 7.36-7.33(1H, m), 6.90(1H, d, J=8.3 Hz), 6.83(1H, s), 6.74(1H, d, #J=8.0 Hz), 5.20(2H, s), 4.31(1H, brt, J=12.2 Hz), 2.35-2.19(2H, m),1.99-1.57(5H, m), 1.45-1.20(3H, m)

MS 555(M + 1) 300 MHz, DMSO-d6 12.77(1H, brs), 8.21(1H, d, J=1.4 Hz),7.92(1H, d, J=8.7 Hz), 7.88(1H, dd, J=8.7, 1.4 Hz), 7.57(2H, d, J=8.7Hz), 7.57-7.27(7H, m), 7.11(2H, d, J=8.7 Hz), 5.07(2H, s), 4.26(1H, m),2.36-2.16(2H, m), 1.98-1.75(4H, m), 1.64(1H, m), 1.49-1.17(3H, m).

MS 581(M + 1) 300 MHz, DMSO-d6 8.32(1H, s), 8.30-8.20(2H, m),8.10-7.98(2H, m), 7.74(2H, d, J=9.0 Hz), 7.60-7.46(5H, m), 7.24(2H, d,J=9.0 Hz), 5.19(2H, s), 4.44-4.30(1H, m), 2.40-2.20(2H, m),2.12-1.78(4H, m), 1.72-1.58(4H, m)

[2011] TABLE 54 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 580(M + 1) 300 MHz, DMSO-d6 8.36-7.90(5H, m), 7.74(2H, d, J=8.6 Hz),7.60-7.40(5H, m), 7.25(2H, d, J=8.7 Hz), 5.14(2H, s), 4.45-4.28(1H, m),2.40-2.15(4H, m), 1.75-1.55(1H, m), 1.55-1.20(3H, m)

MS 514(M + 1) 300 MHz, DMSO-d6 8.22(1H, s), 7.94(1H, d, J=8.4 Hz),7.85(1H, d, J=8.7 Hz), 7.61(2H, d, J=8.7 Hz), 7.25-7.00(6H m), 4.86(2H,s), 4.30(1H, m), 2.89(3H, s), 2.80(3H, s), 2.29(2H, m), 2.00-1.75(4H,m), 1.70-1.55(1H, m), 1.50-1.15(3H, m)

MS 554(M + 1) 300 MHz, DMSO-d6 8.22(1H, s), 7.94(1H, d, J=8.4 Hz),7.85(1H, d, J=8.7 Hz), 7.61(2H, d, J=8.7 Hz), 7.26-7.01(6H, m), 4.84(2H,s), 4.31(1H, m), 3.36(4H, m), 2.29(2H, m), 2.00-1.75(4H, m),1.75-1.15(10H, m)

[2012] TABLE 55 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 560(M + 1) 300 MHz, DMSO-d6 13.00(1H, brs), 8.29(1H, d, J=1.4 Hz),8.15(1H, d, J=8.8 Hz), 7.97(1H, dd, J=1.4 Hz, 8.8 Hz), 7.89(2H, d, J=8.8Hz), 7.80-7.60(5H, m), 7.25(2H, d, J=8.8 Hz), 4.47-3.90(4H, m),3.20-3.10(2H, m), 2.41-1.22(14H, m)

MS 524(M + 1) 300 MHz, DMSO-d6 12.80(1H, brs), 8.23(1H, s), 7.97(1H, d,J=8.5 Hz), 7.87(1H, d, J=8.5 Hz), 7.70-7.17(9H, m), 4.60-4.13(4H, m),3.72-3.40(2H, m), 2.40-1.15(14H, m)

MS 580(M + 1) 300 MHz, DMSO-d6 8.25(1H, s), 8.09-7.92(5H, m), 7.77(1H,s), 7.65(2H, d, J=8.4 Hz), 7.59-7.51(3H, m), 7.43(2H, d, J=8.4 Hz),7.17(2H, d, J=8.7 Hz), 5.10(2H, s), 4.30(1H, m), 2.40-2.15(2H, m),2.10-1.75(4H, m), 1.75-1.55(1H, m), 1.55-1.10(3H, m).

[2013] TABLE 56 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 514(M + 1) 300 MHz, DMSO-d6 8.22(1H, s), 7.95(1H, d, J=8.4 Hz),7.86(1H, d, J=8.4 Hz), 7.69 and 7.18(4H, ABq, J=8.7 Hz), 7.34(1H, t,J=8.0 Hz), 6.80-6.69(3H, m), 4.83(2H, s), 4.31(1H, m), 2.98(3H, s),2.84(3H, s), 2.29(2H, m), # 2.00-1.75(4H, m), 1.70-1.55(1H, m),1.50-1.15(3H, m)

MS 554(M + 1) 300 MHz, DMSO-d6 8.23(1H, s), 7.95 (1H, d, J=8.4 Hz),7.86(1H, d, J=8.7 Hz), 7.69 and 7.18 (4H, ABq, J=8.7 Hz), 7.35(1H, t,J=8.4 Hz), 6.80-6.70(3H, m), 4.82(2H, s), 4.31(1H, m), 3.40(4H, m),2.29(2H, m), 2.00-1.75(4H, m), 1.70-1.15(10H, m)

MS 604(M + 1) 300 MHz, DMSO-d6 12.75(1H, s), 8.23 (1H, d, J=4.4 Hz),7.95 and 7.86(2H, ABq, J=8.6 Hz), 7.69 and 7.19(4H, A′B′q, J=8.6 Hz),7.36(1H, t, J=7.8 Hz), 6.82 (1H, d, J=9.3 Hz), 6.73(1H, s), 6.71 (1H, d,J=7.2 Hz), 4.30(1H, brt, J= # 12.2 Hz), 3.89(2H, d, J=6.0 Hz), 3.59(2H,d, J=11.7 Hz), 2.85 (3H, s), 2.73(2H, t, J=10.5 Hz), 2.41-2.20(2H, m),1.98-1.59(8H, m), 1.46-1.18(5H, m)

[2014] TABLE 57 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 542(M + 1) 300 MHz, DMSO-d6 8.33(1H, s), 8.30(1H, d, J=8.9 Hz),8.06(1H, d, J=8.7 Hz), 7.79(2H, d, J=8.7 Hz), 7.70(2H, d, J=8.7 Hz),7.61(2H, d, J=8.7 Hz), 7.39(2H, d, J=8.8 Hz), 5.28(2H, s), 4.39(1H, m),2.50-2.15(2H, m), 2.15-1.95(2H, m), 1.95- # 1.75(2H, m), 1.75-1.55(1H,m), 1.55-1.15(3H, m).

MS 553(M + 1) (DMSO-d6) δ: 8.23(1H, s), 7.96(1H, d, J=8.6 Hz), 7.86(1H,d, J=8.6 Hz), 7.69(2H, d, J=8.4 Hz), 7.52(1H, s), 7.50-7.30(4H, m),7.18(2H, d, J=8.4 Hz), 6.90(1H, d, J=8.3 Hz), 6.84(1H, s), 6.74(1H, d,J=8.3 Hz), 5.15(2H, s), 4.39- # 4.21(1H, m), 2.39-2.18(2H, m),1.99-1.80(4H, m), 1.71-1.59(1H, m), 1.50-1.20(3H, m)

MS 553(M + 1) (DMSO-d6) δ: 8.26(1H, s), 8.06(1H, d, J=8.7 Hz), 7.92(1H,d, J=8.7 Hz), 7.72(2H, d, J=8.7 Hz), 7.47(4H, s), 7.38(1H, t, J=8.2 Hz),7.20(2H, d, J=8.7 Hz), 6.90(1H, d, J=8.2 Hz), 6.83(1H, s), 6.74(1H, d,J=8.2 Hz), 5.14(2H, s), 2.40- # 2.19(2H, m), 2.04-1.78(4H, m),1.71-1.60(1H, m), 1.50-1.21(3H, m)

[2015] TABLE 58 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 537(M + 1) (DMSO-d6) δ: 12.81(1H, brs), 8.24(1H, s), 7.99(1H, d,J=8.7 Hz), 7.87(1H, d, J=8.7 Hz), 7.69(2H, d, J=8.6 Hz), 7.53-7.47(2H,m), 7.38(1H, t, J=8.2 Hz), 7.26-7.16(4H, m), 6.89(1H, d, J=8.2 Hz),6.82(1H, s), 6.73(1H, d, J=8.2 Hz), 5.11(2H, s), 4.40- # 4.21(1H, m),2.40-2.17(2H, m), 2.01-1.77(4H, m), 1.71-1.59(1H, m), 1.50-1.20(3H, m)

MS 541(M + 1) 300 MHz, DMSO-d6 12.74(1H, brs), 8.21(1H, s), 8.08(2H, d,J=9.0 Hz), 7.93(1H, d, J=8.7 Hz), 7.85(2h, d, J=8.7 Hz), 7.58(2H, d,J=8.7 Hz), 7.13(2H, d, J=8.7 Hz), 6.83(2H, d, J=9.0 Hz), 4.50-4.08(4H,m), 3.68-3.30(2H, m), 2.40-1.23(14H, m)

MS 300 MHz, DMSO-d6 8.39-8.28(2H, m), 8.08(1H, d, J=8.8 Hz), 7.76(2H, d,J=8.7 Hz), 7.29(2H, d, J=8.7 Hz), 7.25-7.13(2H, m), 6.80-6.60(3H, m),4.46-3.98(4H, m), 3.51-3.42(1H, m), 3.20-3.04(1H, m), 2.39-1.20(14H, m)

[2016] TABLE 59 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 553(M + 1) 300 MHz, DMSO-d6 9.59(1H, brs), 8.23(1H, s), 8.04(1H, d,J=8.4 Hz), 7.90(1H, d, J=8.4 Hz), 7.62(2H, d, J=8.7 Hz), 7.39(2H, 2H, d,J=8.7 Hz), 7.18(2H, d, J=8.7 Hz), 6.63(2H, d, J=8.7 Hz), 3.95-3.37(4H,m), 3.51-3.40(1H, m), 3.17-3.02(1H, m), 2.39-1.18(17H, m)

MS 558(M + 1) 300 MHz, DMSO-d6 13.1(1H, brs), 8.33(1H, s), 8.29(1H, d,J=8.8 Hz), 8.06(1H, d, J=8.7 Hz), 7.77(2H, d, J=8.7 Hz), 7.59-7.52(4H,m), 7.35(2H, d, J=8.8 Hz), 5.19(2H, s), 4.39(1H, m), 2.71(3H, s),2.45-2.20(2H, m), 2.20-1.95(2H, m), 1.95-1.75(2H, m), 1.75-1.55(1H, m),1.55-1.15(3H, m).

MS 539(M + 1) 300 MHz, DMSO-d6 8.29(1H, s), 8.26(1H, d, J=8.8 Hz),8.04(1H, d, J=8.7 Hz), 7.73(2H, d, J=8.8 Hz), 7.50-7.41(6H, m), 7.36(2H,d, J=8.8 Hz), 7.18-7.13(2H, m), 6.84(1H, s), 4.33(1H, m), 2.40-2.15(2H,m), 2.15-1.95(2H, m), 1.95-1.75(2H, m), 1.75-1.55(1H, m), 1.55-1.15(3H,m).

[2017] TABLE 60 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 582(M + 1) 300 MHz, DMSO-d6 8.32(1H, s), 8.27(1H, d, J=9.0 Hz),8.07-8.00(3H, m), 7.79-7.70(3H, m), 7.51(2H, d, J=8.1 Hz), 7.40(2H, d,J=8.4 Hz), 7.18(2H, d, J=8.7 Hz), 4.99(2H, s), 4.34(1H, m),2.40-2.15(2H, m), 2.15-1.95(2H, m), 1.95- # 1.75(2H, m), 1.75-1.55(1H,m), 1.55-1.15(3H, m).

MS 513(M + 1) 300 MHz, DMSO-d6 8.24(1H, d, J=4.4 Hz), 7.98 and 7.88(2H,ABq, J=8.6 Hz), 7.70 and 7.19(4H, A′B′q, J=8.4 Hz), 7.35(1H, t, J=8.4Hz), 6.86(1H, d, J=8.1 Hz), 6.79(1H, s), 6.71(1H, d, J=8.1 Hz),4.65-4.53(1H, m), 4.31(1H, brt, J=12.2 Hz), 3.88- # 3.78(2H, m),3.48(2H, t, J=9.0 Hz), 2.39-2.19(2H, m), 1.02-1.71(6H, m), 1.70-1.50(3H,m), 1.46-1.19(3H, m)

MS 587(M + 1) 300 MHz, DMSO-d6 12.75(1H, s), 8.23(1H, s), 7.96 and7.87(2H, ABq, J=8.7 Hz), 7.84-7.66(6H, m), 7.38(1H, t, J=8.4 Hz),7.18(2H, d, J=8.4 Hz), 6.91(1H, d, J=9.0 Hz), 6.84(1H, s), 6.74(1H, d,J=8.1 Hz), 5.26(2H, s), 4.31(1H, brt, J=12.2 Hz), 2.40- # 2.20(2H, m),1.99-1.76(4H, m), 1.69-1.58(1H, m), 1.45-1.20(3H, m)

[2018] TABLE 61 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 540(M + 1) 300 MHz, DMSO-d6 8.29(1H, s), 8.15 and 7.47(2H, ABq, J=9.0Hz), 7.77 and 7.24(4H, ABq, J=8.9 Hz), 7.39(1H, t, J=7.8 Hz), 6.84 (1H,d, J=9.3 Hz), 6.76(1H, s), 6.75 (1H, d, J=9.5 Hz), 4.36(1H, brt, J=12.2Hz), 3.89 (2H, d, J=6.0 Hz), 3.42(2H, d, J= # 10.8 Hz), 3.04-2.88(2H,m), 2.78-2.60(1H, m), 2.71(2H, d, J=4.8 Hz), 2.38-2.20(2H, m),2.07-1.80(7H, m), 1.70-1.20(5H, m)

MS 575(M + 1) 300 MHz, DMSO-d6 8.22(1H, s), 7.93 and 7.87(2H, ABq, J=8.6Hz), 7.68 and 7.17(4H, A′B′q, J=8.7 Hz), 7.43-7.33(5H, m), 6.87(1H, d,J=8.1 Hz), 7.18(2H, d, J=8.4 Hz), 6.91(1H, d, J=9.0 Hz), 6.81(1H, s),6.72 (1H, d, J=8.0 Hz), 5.08(2H, s), 4.36(1H, # brt, J=12.2 Hz),2.37-2.20(2H, m), 1.98-1.78(4H, m), 1.69-1.60(1H, m), 1.41-1.21(3H, m),1.28(9H, s)

MS 553(M + 1) 300 MHz, DMSO-d6 8.23(1H, s), 7.95 and 7.86(2H, ABq, J=8.4Hz), 7.69 and 7.19(4H, A′B′q, J=8.7 Hz), 7.62-7.36(5H, m), 6.90(1H, d,J=8.1 Hz), 6.84(1H, s), 6.76(1H, d, J=8.1 Hz), 5.19(2H, s), 4.31(1H,brt, J=12.2 Hz), 2.40-2.19(2H, m), # 1.99-1.76(4H, m), 1.68-1.55(1H, m),1.50-1.18(3H, m)

[2019] TABLE 62 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 490(M + 1) 300 MHz, DMSO-d6 8.94(1H, d, J=2.1 Hz), 8.60(1H, dd,J=4.8, 1.5 Hz), 8.23(1H, d, J=1.5 Hz), 8.12(1H, dt, J=8.1, 2.1 Hz),7.93(1H, d, J=8.7 Hz), 7.87(1H, dd, J=8.7, 1.5 Hz), 7.70(1H, d, J=8.7Hz), 7.67-7.54(3H, m), 7.50(1H, dd, J=8.1, 4.8 Hz), 7.25(2H, d, J=8.7Hz), 7.21(1H, m), # 4.31(1H, m), 2.38-2.19(2H, m), 2.00-1.78(4H, m),1.65(1H, m), 1.48-1.22(3H, m).

MS 523(M + 1) 300 MHz, DMSO-d6 12.75(1H, brs), 8.23(1H, s), 7.95(1H, d,J=8.7 Hz), 7.86(1H, d, J=8.7 Hz), 7.73(2H, d, J=8.4 Hz), 7.71(2H, d,J=8.4 Hz), 7.63-7.39(2H, m), 7.52(2H, d, J=8.4 Hz), 7.24(2H, d, J=8.4Hz), 7.18(1H, m), 4.31(1H, m), 2.39-2.20(2H, m), 2.00- # 1.76(4H, m),1.65(1H, m), 1.49-1.18(3H, m).

MS 519(M + 1) 300 MHz, DMSO-d6 12.77(1H, s), 8.23(1H, d, J=1.4 Hz),7.95(1H, d, J=8.6 Hz), 7.86(1H, dd, J=8.6, 1.4 Hz), 7.70(2H, d, J=8.7Hz), 7.64(2H, d, J=8.8 Hz), 7.56-7.48(2H, m), 7.40(1H, s), 7.23(2H, d,J=8.7 Hz), 7.10(1H, m), 7.03(2H, d, J=8.8 Hz), 4.31(1H, m), 3.80(3H, s),2.48- # 2.20(2H, m), 2.00-1.88(4H, m), 1.66(1H, m), 1.50-1.21(3H, m).

[2020] TABLE 63 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 602(M + 1) (DMSO-d6) δ: 12.80(1H, brs), 8.23(1H, s), 8.04(1H, d,J=8.6 Hz), 7.96(3H, d, J=8.6 Hz), 7.86(1H, d, J=8.7 Hz), 7.63(2H, d,J=8.6 Hz), 7.25(2H, d, J=8.6 Hz), 5.50(2H, s), 4.36-4.21(1H, m),3.27(3H, s), 2.74(3H, s), 2.40-2.19(2H, m), 1.99-1.79(4H, m),1.71-1.60(1H, m), 1.49-1.19(3H, m)

MS 558(M + 1) 300 MHz, DMSO-d6 12.9(1H, brs), 8.25(1H, s), 8.04(1H, d,J=8.7 Hz), 7.91(1H, d, J=8.6 Hz), 7.72(2H, d, J=8.5 Hz), 7.67(2H, d,J=8.7 Hz), 7.56(2H, d, J=8.5 Hz), 7.26(2H, d, J=8.7 Hz), 5.45(2H, s),4.31(1H, m), 2.71(3H, s), 2.40-2.15(2H, m), 2.05-1.80(4H, m),1.75-1.55(1H, m), 1.55-1.15(3H, m).

MS 544(M + 1) 300 MHz, DMSO-d6 8.21(1H, d, J=1.5 Hz), 7.93(1H, d, J=9.0Hz), 7.84(1H, dd, J=9.0, 1.5 Hz), 7.56(2H, d, J=8.7 Hz), 7.42-7.30(4H,m), 7.12(2H, d, J=8.7 Hz), 4.53(1H, brs), 4.36-4.20(1H, m), 3.55(2H,brs), 3.00-2.90(1H, m), 2.70-2.58(1H, m), 2.40-1.10(18H, m)

[2021] TABLE 64 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 540(M + 1) 300 MHz, DMSO-d6 12.76(1H, s), 8.23(1H, s), 7.96 and7.87(2H, ABq, J=8.9 Hz), 7.69 and 7.19(4H, A′B′q, J=8.6 Hz), 7.55(1H,s), 7.37(1H, J=8.1 Hz), 6.91(1H, d, J=7.8 Hz), 6.85(1H, s), 6.74(1H, d,J=7.5 Hz), 5.13(2H, s), 4.31(1H, brt, J=12.2 Hz), 2.65(3H, s), 2.41- #2.20(2H, m), 2.00-1.74(4H, m), 1.70-1.59(1H, m), 1.58-1.20(3H, m)

MS 554(M + 1) 300 MHz, DMSO-d6 8.23(1H, s), 7.96 and 7.86(2H, ABq, J=8.6Hz), 7.69 and 7.18(4H, A′B′q, J=8.7 Hz), 7.37(1H, t, J=8.2 Hz), 6.87(1H,d, J=8.2 Hz), 6.82(1H, s), 6.75(1H, d, J=8.0 Hz), 5.24(2H, s), 4.32(1H,brt, J=12.2 Hz), 2.58(3H, s), 2.38-2.20(2H, m), 2.30(3H, s),2.00-1.79(4H, m), # 1.70-1.59(1H, m), 1.44-1.20(3H, m)

MS 557(M + 1) 300 MHz, DMSO-d6 12.88(1H, brs), 8.25(s, 1H),8.07-7.57(11H, m), 7.26(2H, d, J=8.7), 7.24(1H, m), 4.34(1H, m),2.30-2.20(2H, m), 2.03-1.78(4H, m), 1.64(1H, m), 1.49-1.19(3H, m)

[2022] TABLE 65 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 544(M + 1) 300 MHz, DMSO-d6 10.96(1H, brs), 8.21(1H, d, J=1.4 Hz),7.93(1H, d, J=8.7 Hz), 7.84(1H, dd, J=8.7, 1.4 Hz), 7.76-7.40(7H, m),7.18(2H, d, J=8.0 Hz), 4.24-4.16(2H, m), 2.40-1.12(18H, m)

MS 544(M + 1) (DMSO-d6) δ: 8.22(1H, s), 8.07(1H, d, J=8.4 Hz), 7.92(1H,d, J=8.4 Hz), 7.54(2H, d, J=8.7 Hz), 7.40(2H, d, J=8.4 Hz), 7.30(2H, d,J=8.4 Hz), 7.14(2H, d, J=8.7 Hz), 4.61(2H, s), 4.48-4.32(1H, m),3.82(1H, brd, J=12.3 Hz), 3.65-3.47(2H, m), 3.10(brdd, # J=8.4, 12.3Hz), 2.40-2.20(2H, m), 2.09-1.76(6H, m), 1.71-1.16(6H, m)

MS 580(M + 1) (DMSO-d6) δ: 12.83(1H, brs), 8.21(1H, s), 8.10(1H, brs),7.01-7.91(2H, m), 7.89-7.82(2H, m), 7.75(1H, d, J=8.0 Hz), 7.59(2H, d,J=8.7 Hz), 7.53(4H, s), 7.46(1H, brs), 7.12(2H, d, J=8.7 Hz), 7.23(2H,s), 4.35-4.17(1H, m), 2.38-2.20(2H, m), 1.99-1.79(4H, m), #1.71-1.59(1H, m), 1.48-1.18(3H, m)

[2023] TABLE 66 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 544(M + 1) 300 MHz, DMSO-d6 8.33 and 8.08(2H, ABq, J=8.7 Hz),8.31(1H, m), 7.66 and 7.26(4H, A′B′q, J=9.2 Hz), 7.42 and 7.39(4H,A″B″q, J=8.7 Hz), 4.57(2H, s), 4.50(1H, brt, J=12.2 Hz), 3.85-3.62(3H,m), 3.28-3.16(2H, m), 2.42-2.23(2H, m), 2.14-1.81(6H, m), 1.72-1.25(6H,m)

MS 554(M + 1) 300 MHz, DMSO-d6 8.43(1H, d, J=5.0 Hz), 8.23(1H, s), 7.96and 7.86(2H, ABq, J=8.6 Hz), 7.69 and 7.18(4H, A′B′q, J=8.6 Hz),7.57(1H, s), 7.47(1H, d, J=5.0 Hz), 7.40(2H, t, J=8.2 Hz), 6.91(1H, d,J=8.3 Hz), 6.85(1H, s), 6.77(1H, d, J=7.9 Hz), 5.25(2H, s), 4.31(1H,brt, # J=12.2 Hz), 2.40-2.19(2H, m), 1.99-1.75(4H, m), 1.73-1.57(1H, m),1.49-1.19(3H, m)

MS 567(M + 1) 300 MHz, DMSO-d6 12.80(1H, brs), 8.22(1H, s), 7.94(1H, d,J=8.6 Hz), 7.87(1H, d, J=8.6 Hz), 7.60(2H, d, J=8.7 Hz), 7.32(2H, d,J=8.7 Hz), 7.17(2H, d, J=8.7 Hz), 6.70(2H, d, J=8.7 Hz), 4.35-3.97(4H,m), 3.62-3.11(2H, m), 2.96(6H, s), 2.39-1.12(4H, m)

[2024] TABLE 67 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 608(M + 1) 300 MHz, DMSO-d6 8.25(1H, s), 8.20(1H, s), 8.04(1H, dd,J=8.1, 1.8 Hz), 7.92(1H, d, J=8.1 Hz), 7.84(1H, d, J=9.9 Hz),7.62-7.50(7H, m), 7.12(2H, d, J=8.7 Hz), 5.14(2H, s), 4.36(2H, q, J=6.9Hz), 4.30-4.20(1H, m), 2.38-2.18(2H, m), 1.98-1.18(8H, m), 1.35(3H, t,J=6.9 Hz)

MS 481(M + 1) 300 MHz, DMSO-d6 8.35(1H, s), 8.27(1H, d, J=8.7 Hz),8.05(1H, d, J=9.0 Hz), 7.87(2H, d, J=8.7 Hz), 7.74(1H, t, J=8.1 Hz),7.64(1H, d, J=7.8 Hz), 7.59-7.50(2H, m), 7.36(2H, d, J=8.7 Hz), 4.39(1H,m), 2.40-2.15(2H, m), 2.15-1.95(2H, m), 1.95-1.75(2H, m), 1.75-1.55(1H,m), 1.55-1.20(3H, m).

MS 595(M + 1) 300 MHz DMSO-d6 12.78(1H, brs), 8.23(1H, d, J=1.5 Hz),7.96(1H, d, J=8.7 Hz), 7.87(1H, dd, J=8.7, 1.5 Hz), 7.75(2H, d, J=8.4Hz), 7.63(2H, d, J=8.4 Hz), 7.52(2H, d, J=8.4 Hz), 7.24(2H, d, J=8.4Hz), 5.47(2H, s), 4.29(1H, m), 2.97(6H, brs), 2.72(3H, s), 2.39-2.16(2H,m), 2.00-1.78(4H, m), # 1.71-1.59(1H, m), 1.49-1.17(3H, m).

[2025] TABLE 68 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS 608(M + 1) 300 MHz, DMSO-d6 12.8(1H, brs), 8.22(1H, s), 7.96(1H, d,J=8.7 Hz), 7.86(1H, d, J=8.6 Hz), 7.70(1H, s), 7.59(2H, d, J=8.7 Hz),7.53-7.50(5H, m), 7.42(1H, d, J=7.9 Hz), 7.12(2H, d, J=8.7 Hz), 5.11(2H,s), 4.27(1H, m), 3.01(3H, brs), 2.97(3H, brs), 2.40-2.15(2H, m), 2.00- #1.75(4H, m), 1.75-1.55(1H, m), 1.50-1.15(3H, m).

MS 553(M + 1 − HCl) DMSO-d6 13.20(1H, brs), 8.99(1H, s), 8.32(1H, s),8.25(1H, d, J=8.8 Hz), 8.04(1H, d, J=8.6 Hz), 7.79-7.74(4H, m), 7.60(2H,d, J=8.5 Hz), 7.30(2H, d, J=8.7 Hz), 5.26(2H, s), 4.36(1H, m), 2.72(3H,s), 2.50-2.15(2H, m), 2.15-1.95(2H, m), 1.95-1.75(2H, m), 1.75-1.55(1H,m), 1.55-1.15(3H, m).

MS 538(M + 1 − 2HCl) DMSO-d6 8.77(1H, d, J=3.6 Hz), 8.36-8.26(3H, m),8.08(1H, d, J=8.8 Hz), 7.79(2H, d, J=8.7 Hz), 7.72-7.64(3H, m), 7.58(2H,d, J=8.4 Hz), 7.30(2H, d, J=8.7 Hz), 5.26(2H, s), 4.38(1H, m),2.50-2.15(2H, m), 2.15-1.95(2H, m), 1.95-1.75(2H, m), 1.75-1.55(1H, m),1.55-1.15(3H, m).

[2026] TABLE 69 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS APCI-Ms 538(M + 1) 300 MHz, DMSO-d6 12.74(1H, brs), 8.67(1H, dd,J=3.1, 1.6 Hz), 8.21(1H, d, J=1.6 Hz), 7.93(1H, d, J=8.6 Hz),7.90-7.80(2H, m), 7.60-7.50(7H, m), 7.09(2H, d, J=8.7 Hz), 5.16(2H, s),4.26(1H, m), 2.40-2.20(2H, m), 2.00-1.60(5H, m), 1.50-1.20(3H, m)

MS APCI-Ms 555(M + 1) 300 MHz, DMSO-d-6 8.40-7.40(11H, m), 2.95,2.81(3H, each d, J=4.7 Hz), 2.40-2.20(2H, m), 2.10-1.80(4H, m),1.70-1.60(1H, m), 1.50-1.20(3H, m)

MS FAB-Ms 605(M + 1) 300 MHz, DMSO-d6 8.21(1H, s), 8.15(1H, d, J=9.5Hz), 8.02(1H, s), 8.00-7.80(3H, m), 7.70-7.50(6H, m), 7.12(2H, d, J=8.7Hz), 5.16(2H, s), 4.28(1H, m), 2.40-2.20(2H, m), 2.00-1.80(4H, m),1.65(1H, m), 1.50-1.20(3H, m)

[2027] TABLE 70 Example No. Purity >90% (NMR) 1H NMR(δ) ppm

MS APCI-Ms 521(M + 1) 300 MHz, DMSO-d6 12.80(1H, brs), 8.54(1H, s),8.25(1H, s), 7.98 and 7.88(2H, Abq, J=8.6 Hz), 7.76(2H, d, J=8.6 Hz),7.53-7.31(3H, m), 6.61(1H, s), 5.46(2H, s), 4.32(1H, brt), 2.40-2.20(2H,m), 2.02-1.79(4H, m), 1.69-1.59(1H, m), 1.48-1.19(3H, m)

MS APCI-Ms 522(M + 1) 300 MHz, DMSO-d6 12.79(1H, brs), 8.60(2H, d, J=1.5Hz), 8.53(1H, s), 8.25(1H, s), 7.98 and 7.85(2H, ABq, J=9.4 Hz),7.76(2H, d, J=9.0 Hz), 7.44(4H, d, J=6.5 Hz), 6.69(1H, s), 5.53(2H, s),4.32(1H, brt), 2.40-2.19(2H, m), # 2.03-1.82(4H, m), 1.72-1.61(1H, m),1.42-1.22(3H, m)

MS APCI-Ms 525(M + 1) 300 MHz, DMSO-d6 8.90(1H, s), 8.32(1H, s),8.28(1H, s), 8.25(1H, d, J=8.3 Hz), 8.05(1H, d, J=8.8 Hz), 7.96(1H, s),7.93(1H, d, J=8.8 Hz), 7.83(1H, d, J=8.4 Hz), 7.68-7.59(2H, m), 7.54(2H,d, J=8.8 Hz), 4.37(1H, brt), 2.30(2H, m), 2.00(2H, m), # 1.88(2H, m),1.67(1H, m), 1.5-1.2(3H, m)

[2028] TABLE 71 Ex. No. Formula MS 1001

364 (M + H) 1002

454 (M + H) 1003

398 (M + H) 1004

357 (M + H) 1005

322 (M + H) 1006

385 (M + H)

[2029] TABLE 72 Ex. No. Formula MS 1007

357 (M + H) 1008

416 (M + H) 1009

310 (M + H) 1010

390 (M + H) 1011

395 (M + H) 1012

366 (M + H)

[2030] TABLE 73 Ex. No. Formula MS 1013

374 (M + H) 1014

382 (M + H) 1015

350 (M + H) 1016

402 (M + H) 1017

414 (M + H) 1018

340 (M + H)

[2031] TABLE 74 Ex. No. Formula MS 1019

350 (M + H) 1020

380 (M + H) 1021

366 (M + H) 1022

378 (M + H) 1023

402 (M + H)

[2032] TABLE 75 Ex. No. Formula MS 1024

518 (M + H) 1025

408 (M + H) 1026

336 (M + H) 1027

408 (M + H) 1028

366 (M + H) 1029

362 (M + H)

[2033] TABLE 76 Ex. No. Formula MS 1030

473 (M + H) 1031

338 (M + H) 1032

307 (M + H) 1033

406 (M + H) 1034

466 (M + H) 1035

412 (M + H)

[2034] TABLE 77 Ex. No. Formula MS 1036

412 (M + H) 1037

428 (M + H) 1038

466 (M + H) 1039

406 (M + H) 1040

417 (M + H) 1041

440 (M + H)

[2035] TABLE 78 Ex. No. Formula MS 1042

417 (M + H) 1043

440 (M + H) 1044

312 (M + H) 1045

423 (M + H) 1046

352 (M + H) 1047

307 (M + H)

[2036] TABLE 79 Ex. No. Formula MS 1048

374 (M + H) 1049

398 (M + H) 1050

326 (M + H) 1051

442 (M + H) 1052

518 (M + H)

[2037] TABLE 80 Ex. No. Formula MS 1053

442 (M + H) 1054

376 (M + H) 1055

442 (M + H) 1056

352 (M + H) 1057

367 (M + H) 1058

367 (M + H)

[2038] TABLE 81 Ex. No. Formula MS 1059

364 (M + H) 1060

324 (M + H) 1061

352 (M + H) 1062

357 (M + H) 1063

360 (M + H) 1064

351 (M + H)

[2039] TABLE 82 Ex. No. Formula MS 1065

351 (M + H) 1066

366 (M + H) 1067

367 (M + H) 1068

364 (M + H) 1069

350 (M + H) 1070

306 (M + H)

[2040] TABLE 83 Ex. No. Formula MS 1071

365 (M + H) 1072

455 (M + H) 1073

399 (M + H) 1074

358 (M + H) 1075

337 (M + H) 1076

386 (M + H)

[2041] TABLE 84 Ex. No. Formula MS 1077

358 (M + H) 1078

417 (M + H) 1079

311 (M + H) 1080

391 (M + H) 1081

396 (M + H) 1082

367 (M + H)

[2042] TABLE 85 Ex. No. Formula MS 1083

375 (M + H) 1084

351 (M + H) 1085

383 (M + H) 1086

403 (M + H) 1087

415 (M + H) 1088

341 (M + H)

[2043] TABLE 86 Ex. No. Formula MS 1089

351 (M + H) 1090

381 (M + H) 1091

367 (M + H) 1092

379 (M + H) 1093

403 (M + H)

[2044] TABLE 87 Ex. No. Formula MS 1094

519 (M + H) 1095

409 (M + H) 1096

337 (M + H) 1097

409 (M + H) 1098

367 (M + H) 1099

363 (M + H)

[2045] TABLE 88 Ex. No. Formula MS 1100

474 (M + H) 1101

339 (M + H) 1102

308 (M + H) 1103

467 (M + H) 1104

413 (M + H) 1105

413 (M + H)

[2046] TABLE 89 Ex. No. Formula MS 1106

429 (M + H) 1107

467 (M + H) 1108

1109

1110

441 (M + H) 1111

418 (M + H)

[2047] TABLE 90 Ex. No. Formula MS 1112

313 (M + H) 1113

308 (M + H) 1114

375 (M + H) 1115

399 (M + H) 1116

327 (M + H) 1117

443 (M + H)

[2048] TABLE 91 Ex. No. Formula MS 1118

519 (M + H) 1119

443 (M + H) 1120

377 (M + H) 1121

443 (M + H) 1122

353 (M + H)

[2049] TABLE 92 Ex. No. Formula MS 1123

368 (M + H) 1124

368 (M + H) 1125

365 (M + H) 1126

325 (M + H) 1127

353 (M + H) 1128

358 (M + H)

[2050] TABLE 93 Ex. No. Formula MS 1129

361 (M + H) 1130

352 (M + H) 1131

352 (M + H) 1132

367 (M + H) 1133

368 (M + H) 1134

365 (M + H)

[2051] TABLE 94 Ex. No. Formula MS 1135

351 (M + H) 1136

307 (M + H) 1137

385 (M + H) 1138

365 (M + H) 1139

467 (M + H) 1140

387 (M + H)

[2052] TABLE 95 Ex. No. Formula MS 1141

322 (M + H) 1142

364 (M + H) 1143

323 (M + H) 1144

363 (M + H) 1145

484 (M + H) 1146

385 (M + H)

[2053] TABLE 96 Ex. No. Formula MS 1147

427 (M + H) 1148

420 (M + H) 1149

508 (M + H) 1150

458 (M + H) 1151

458 (M + H)

[2054] TABLE 97 Ex. No. Formula MS 1152

474 (M + H) 1153

458 (M + H) 1154

508 (M + H) 1155

454 (M + H)

[2055] TABLE 98 Ex. No. Formula MS 1156

470 (M + H) 1157

496 (M + H) 1158

482 (M + H) 1159

448 (M + H) 1160

488 (M + H)

[2056] TABLE 99 Ex. No. Formula MS 1161

468 (M + H) 1162

447 (M + H) 1163

466 (M + H) 1164

526 (M + H) 1165

420 (M + H)

[2057] TABLE 100 Ex. No. Formula MS 1166

490 (M + H) 1167

435 (M + H) 1168

436 (M + H) 1169

436 (M + H) 1170

404 (M + H) 1171

406 (M + H)

[2058] TABLE 101 Ex. No. Formula MS 1172

392 (M + H) 1173

420 (M + H) 1174

406 (M + H) 1175

420 (M + H) 1176

523 (M + H) 1177

406 (M + H)

[2059] TABLE 102 Ex. No. Formula MS 1178

447 (M + H) 1179

433 (M + H) 1180

509 (M + H) 1181

513 (M + H)

[2060] TABLE 103 Ex. No. Formula MS 1182

497 (M + H) 1183

496 (M + H) 1184

418 (M + H) 1185

508 (M + H) 1186

490 (M + H)

[2061] TABLE 104 Ex. No. Formula MS 1187

441 (M + H) 1188

455 (M + H) 1189

455 (M + H) 1190

513 (M + H) 1191

504 (M + H) 1192

494 (M + H)

[2062] TABLE 105 Ex. No. Formula MS 1193

512 (M + H) 1194

504 (M + H) 1195

516 (M + H) 1196

497 (M + H) 1197

456 (M + H) 1198

509 (M + H)

[2063] TABLE 106 Ex. No. Formula MS 1199

483 (M + H) 1200

427 (M + H) 1201

427 (M + H) 1202

477 (M + H) 1203

519 (M + H) 1204

440 (M + H)

[2064] TABLE 107 Ex. No. Formula MS 1205

454 (M + H) 1206

325 (M + H) 1207

341 (M + H) 1208

385 (M + H) 1209

363 (M + H) 1210

332 (M + H)

[2065] TABLE 108 Ex. No. Formula MS 1211

351 (M + H) 1212

335 (M + H) 1213

349 (M + H) 1214

375 (M + H) 1215

375 (M + H) 1216

367 (M + H)

[2066] TABLE 109 Ex. No. Formula MS 1217

433 (M + H) 1218

391 (M + H) 1219

337 (M + H) 1220

385 (M + H) 1221

341 (M + H) 1222

332 (M + H)

[2067] TABLE 110 Ex. No. Formula MS 1223

395 (M + H) 1224

375 (M + H) 1225

351 (M + H) 1226

321 (M + H) 1227

426 (M + H) 1228

460 (M + H)

[2068] TABLE 111 Ex. No. Formula MS 1229

442 (M + H) 1230

468 (M + H) 1231

456 (M + H) 1232

494 (M + H) 1233

451 (M + H) 1234

468 (M + H)

[2069] TABLE 112 Ex. No. Formula MS 1235

498 (M + H) 1236

476 (M + H) 1237

502 (M + H) 1238

505 (M + H) 1239

469 (M + H)

[2070] TABLE 113 Ex. No. Formula MS 1240

483 (M + H) 1241

408 (M + H) 1242

460 (M + H) 1243

468 (M + H) 1244

494 (M + H) 1245

454 (M + H)

[2071] TABLE 114 Ex. No. Formula MS 1246

468 (M + H) 1247

498 (M + H) 1248

482 (M + H) 1249

468 (M + H) 1250

460 (M + H)

[2072] TABLE 115 Ex. No. Formula MS 1251

442 (M + H) 1252

468 (M + H) 1253

456 (M + H) 1254

494 (M + H)

[2073] TABLE 116 Ex. No. Formula MS 1255

451 (M + H) 1256

468 (M + H) 1257

498 (M + H) 1258

470 (M + H)

[2074] TABLE 117 Ex. No. Formula MS 1259

476 (M + H) 1260

502 (M + H) 1261

505 (M + H) 1262

469 (M + H)

[2075] TABLE 118 Ex. No. Formula MS 1263

483 (M + H) 1264

408 (M + H) 1265

460 (M + H) 1266

468 (M + H)

[2076] TABLE 119 Ex. No. Formula MS 1267

494 (M + H) 1268

454 (M + H) 1269

468 (M + H) 1270

498 (M + H)

[2077] TABLE 120 Ex. No. Formula MS 1271

482 (M + H) 1272

468 (M + H) 1273

494 (M + H) 1274

484 (M + H)

[2078] TABLE 121 Ex. No. Formula MS 1275

519 (M + H) 1276

427 (M + H) 1277

456 (M + H) 1278

516 (M + H)

[2079] TABLE 122 Ex. No. Formula MS 1279

436 (M + H) 1280

426 (M + H) 1281

440 (M + H) 1282

454 (M + H) 1283

468 (M + H)

[2080] TABLE 123 Ex. No. Formula MS 1284

482 (M + H) 1285

406 (M + H) 1286

420 (M + H) 1287

508 (M + H) 1288

508 (M + H)

[2081] TABLE 124 Ex. No. Formula MS 1289

509 (M − H) 1290

455 (M + H) 1291

494 (M + H) 1292

418 (M + H)

[2082] TABLE 125 Ex. No. Formula MS 1293

490 (M + H) 1294

496 (M + H) 1295

477 (M + H) 1296

508 (M + H) 1297

470 (M + H)

[2083] TABLE 126 Ex. No. Formula MS 1298

435 (M + H) 1299

488 (M + H) 1300

454 (M + H) 1301

504 (M + H)

[2084] TABLE 127 Ex. No. Formula MS 1302

513 (M + H) 1303

399 (M + H) 1304

530 (M + H) 1305

504 (M + H) 1306

440 (M + H)

[2085] TABLE 128 Ex. No. Formula MS 1307

494 (M + H) 1308

508 (M + H) 1309

518 (M + H) 1310

532 (M + H) 1311

522 (M + H)

[2086] TABLE 129 Ex. No. Formula MS 1312

546 (M − H) 1313

484 (M + H) 1314

517 (M + H) 1315

488 (M + H) 1316

481 (M + H)

[2087] TABLE 130 Ex. No. Formula MS 1317

413 (M + H) 1318

423 (M + H) 1319

504 (M − H) 1320

510 (M + H) 1321

522 (M + H) 1322

522 (M + H)

[2088] TABLE 131 Ex. No. Formula MS 1323

484 (M − H) 1324

449 (M + H) 1325

502 (M + H) 1326

491 (M + H) 1327

496 (M + H)

[2089] TABLE 132 Ex. No. Formula MS 1328

497 (M + H) 1329

470 (M + H) 1330

530 (M + H) 1331

502 (M + H) 1332

522 (M + H)

[2090] TABLE 133 Ex. No. Formula MS 1333

491 (M + H) 1334

536 (M + H) 1335

547 (M + H) 1336

484 (M + H) 1337

484 (M + H) 1338

498 (M + H)

[2091] TABLE 134 Ex. No. Formula MS 1339

528 (M + H) 1340

498 (M + H) 1341

514 (M + H) 1342

513 (M + H) 1343

488 (M + H) 1344

502 (M + H)

[2092] TABLE 135 Ex. No. Formula MS 1345

488 (M + H) 1346

502 (M + H) 1347

499 (M + H) 1348

480 (M + H) 1349

522 (M + H) 1350

546 (M + H)

[2093] TABLE 136 Ex. No. Formula MS 1351

482 (M + H) 1352

484 (M + H) 1353

609 (M + H) 1354

532 (M + H) 1355

480 (M + H) 1356

566 (M + H)

[2094] TABLE 137 Ex. No. Formula MS 1357

602 (M + H) 1358

596 (M + H) 1359

491 (M + H) 1360

491 (M + H) 1361

491 (M + H) 1362

496 (M + H)

[2095] TABLE 138 Ex. No. Formula MS 1363

512 (M + H) 1364

494 (M + H) 1365

488 (M + H) 1366

481 (M + H) 1367

524 (M + H) 1368

497 (M + H)

[2096] TABLE 139 Ex. No. Formula MS 1369

472 (M + H) 1370

469 (M − H) 1371

470 (M + H) 1372

469 (M + H) 1373

494 (M + H) 1374

458 (M + H)

[2097] TABLE 140 Ex. No. Formula MS 1375

612 (M + H) 1376

554 (M + H) 1377

542 (M + H) 1378

526 (M + H) 1379

496 (M + H) 1380

510 (M + H)

[2098] TABLE 141 Ex. No. Formula MS 1381

540 (M + H) 1382

525 (M + H) 1383

558 (M + H) 1384

523 (M + H) 1385

539 (M + H)

[2099] TABLE 142 Ex. No. Formula MS 1386

533 (M + H) 1387

500 (M + H) 1388

485 (M + H) 1389

523 (M + H) 1390

512 (M + H)

[2100] TABLE 143 Ex. No. Formula No. 1391

540 (M + H) 1392

527 (M + H) 1393

525 (M + H) 1394

507 (M + H) 1395

491 (M + H) 1396

506 (M + H)

[2101] TABLE 144 Ex. No. Formula MS 1397

522 (M + H) 1398

538 (M + H) 1399

522 (M + H) 1400

530 (M + H) 1401

600 (M + H) 1402

504 (M + H)

[2102] TABLE 145 Ex. No. Formula MS 1403

534 (M + H) 1404

475 (M + H) 1405

472 (M + H) 1406

455 (M + H) 1407

469 (M + H) 1408

547 (M + H)

[2103] TABLE 146 Ex. No. Formula MS 1409

529 (M + H) 1410

435 (M + H) 1411

504 (M + H) 1412

469 (M + H) 1413

522 (M + H) 1414

488 (M + H)

[2104] TABLE 147 Ex. No. Formula MS 1415

502 (M + H) 1416

488 (M + H) 1417

502 (M + H) 1418

455 (M--H) 1419

455 (M + H) 1420

522 (M + H)

[2105] TABLE 148 Ex. No. Formula MS 1421

469 (M + H) 1422

536 (M--H) 1423

510 (M + H) 1424

494 (M + H) 1425

458 (M + H)

[2106] TABLE 149 Ex. No. Formula MS 1426

612 (M + H) 1427

526 (M + H) 1428

480 (M + H) 1429

441 (M + H) 1430

511 (M + H)

[2107] TABLE 150 Ex. No. Formula MS 1431

530 (M + H) 1432

497 (M + H) 1433

441 (M--H) 1434

491 (M + H) 1435

491 (M + H) 1436

491 (M + H)

[2108] TABLE 151 Ex. No. Formula MS 1437

524 (M + H) 1438

508 (M + H) 1439

474 (M--H) 1440

490 (M + H) 1441

508 (M + H) 1442

474 (M + H)

[2109] TABLE 152 Ex. No. Formula MS 1443

516 (M + H) 1444

600 (M + H) 1445

504 (M + H) 1446

534 (M + H) 1447

475 (M + H)

[2110] TABLE 153 Ex. No. Formula MS 1448

530 (M + H) 1449

440 (M + H) 1450

490 (M + H) 1451

474 (M + H) 1452

441 (M + H) 1453

508 (M--H)

[2111] TABLE 154 Ex. No. Formula MS 1454

455 (M + H) 1455

522 (M + H) 1456

496 (M + H) 1457

516 (M + H) 1458

426 (M + H) 1459

482 (M + H)

[2112] TABLE 155 Ex. No. Formula MS 1460

486 (M + H) 1461

516 (M + H) 1462

427 (M + H) 1463

476 (M + H) 1464

460 (M + H) 1465

502 (M--H)

[2113] TABLE 156 Ex. No. Formula MS 1466

586 (M + H) 1467

518 (M + H) 1468

530 (M + H) 1469

598 (M--H) 1470

512 (M + H) 1471

544 (M + H)

[2114] TABLE 157 Ex. No. Formula MS 1472

440 (M--H) 1473

490 (M + H) 1474

474 (M + H) 1475

441 (M + H) 1476

508 (M + H) 1477

455 (M + H)

[2115] TABLE 158 Ex. No. Formula MS 1478

522 (M + H) 1479

496 (M + H) 1480

516 (M + H) 1481

426 (M + H) 1482

482 (M + H)

[2116] TABLE 159 Ex. No. Formula MS 1483

486 (M--H) 1484

516 (M + H) 1485

427 (M + H) 1486

476 (M + H)

[2117] TABLE 160 Ex. No. Formula MS 1487

460 (M--H) 1488

502 (M + H) 1489

586 (M + H) 1490

518 (M + H)

[2118] TABLE 161 Ex. No. Formula MS 1491

530 (M + H) 1492

598 (M + H) 1493

512 (M + H) 1494

544 (M + H)

[2119] TABLE 162 Ex. No. Formula MS 1495

580 (M + H) 1496

550 (M + H) 1497

606 (M + H) 1498

580 (M + H) 1499

550 (M − H)

[2120] TABLE 163 Ex. No. Formula MS 1500

606 (M + H) 1501

630 (M + H) 1502

600 (M + H) 1503

656 (M + H)

[2121] TABLE 164 Ex. No. Formula MS 1504

630 (M + H) 1505

600 (M + H) 1506

656 (M + H) 1507

580 (M + H)

[2122] TABLE 165 Ex. No. Formula MS 1508

550 (M + H) 1509

606 (M + H) 1510

580 (M + H) 1511

550 (M + H) 1512

546 (M + H)

[2123] TABLE 166 Ex. No. Formula MS 1513

516 (M + H) 1514

572 (M + H) 1515

546 (M + H) 1516

516 (M + H) 1517

572 (M + H)

[2124] TABLE 167 Ex. No. Formula MS 1518

602 (M + H) 1519

572 (M + H) 1520

628 (M + H) 1521

606 (M + H)

[2125] TABLE 168 Ex. No. Formula MS 1522

573 (M + H) 1523

606 (M + H) 1524

602 (M + H) 1525

572 (M + H)

[2126] TABLE 169 Ex. No. Formula MS 1526

628 (M + H) 1527

606 (M + H) 1528

606 (M + H) 1529

614 (M + H)

[2127] TABLE 170 Ex. No. Formula MS 1530

584 (M + H) 1531

640 (M + H) 1532

618 (M + H) 1533

614 (M + H) 1534

584 (M + H)

[2128] TABLE 171 Ex. No. Formula MS 1535

640 (M + H) 1536

627 (M + H) 1537

627 (M + H)

[2129] TABLE 172 Ex. No. Formula MS 1538

560 (M + H) 1539

634 (M + H) 1540

593 (M + H) 1541

627 (M + H)

[2130] TABLE 173 Ex. No. Formula MS 1542

627 (M + H) 1543

560 (M + H) 1544

634 (M + H) 1545

593 (M + H)

[2131] TABLE 174 Ex. No. Formula MS 1546

627 (M + H) 1547

627 (M + H) 1548

560 (M + H) 1549

634 (M + H)

[2132] TABLE 175 Ex. No. Formula MS 1550

627 (M + H) 1551

560 (M + H) 1552

532 (M + H) 1553

565 (M + H)

[2133] TABLE 176 Ex. No. Formula MS 1554

599 (M + H) 1555

599 (M + H) 1556

532 (M + H) 1557

532 (M + H)

[2134] TABLE 177 Ex. No. Formula MS 1558

584 (M + H) 1559

570 (M + H)

[2135] TABLE 178 HCV polymerase HCV polymerase Ex. inhibitory activityEx. inhibitory activity No. IC₅₀ [μM] No. IC₅₀ [μM] 2 0.079 67 0.26 60.034 68 0.28 9 0.019 70 0.19 11 0.53 71 0.62 12 0.60 77 0.51 17 0.04781 0.18 20 0.042 82 0.097 26 0.033 83 0.52 30 0.052 85 0.17 43 0.58 860.13 44 0.95 87 0.80 45 0.40 88 0.092 46 0.47 89 0.34 47 0.54 90 0.20 480.44 91 0.53 49 0.94 93 0.16 50 0.54 94 0.084 51 1.0 96 0.25 54 0.56 970.16 55 0.36 98 0.30

[2136] TABLE 179 HCV polymerase HCV polymerase Ex. inhibitory activityEx. inhibitory activity No. IC₅₀ [μM] No. IC₅₀ [μM] 99 0.53 120 0.16 1000.78 121 0.19 101 0.14 122 0.51 103 0.17 123 0.10 104 0.073 124 0.091105 0.076 125 0.12 106 0.40 128 0.14 107 0.11 129 0.12 108 0.21 130 0.16109 0.11 131 0.046 110 0.24 132 0.055 111 0.14 133 0.12 112 0.11 1340.071 113 0.071 139 0.26 114 0.56 140 0.11 115 0.17 141 0.43 116 0.37142 0.055 117 0.075 143 0.053 118 0.14 144 0.19 119 0.13 145 0.088

[2137] TABLE 180 HCV polymerase HCV polymerase Ex. inhibitory activityEx. inhibitory activity No. IC₅₀ [μM] No. IC₅₀ [μM] 146 0.043 167 0.033147 0.31 168 0.078 148 0.038 169 0.15 149 0.15 170 0.048 150 0.24 1710.050 151 0.20 172 0.10 153 0.19 173 0.14 154 0.076 174 0.030 155 0.53175 0.29 156 0.23 176 0.053 157 0.16 177 0.077 158 0.11 178 0.052 1590.13 179 0.63 160 0.24 180 0.11 161 0.062 181 0.71 162 0.43 182 0.021163 0.15 183 0.017 164 0.16 184 0.018 165 0.58 185 0.11 166 0.055 1860.37

[2138] TABLE 181 HCV polymerase HCV polymerase Ex. inhibitory activityEx. inhibitory activity No. IC₅₀ [μM] No. IC₅₀ [μM] 187 0.056 207 0.081188 0.038 208 0.039 189 0.017 209 0.12 190 0.020 210 0.31 191 0.43 2110.059 192 0.22 212 0.23 193 0.13 213 0.10 194 0.52 214 0.059 195 0.023215 0.078 196 0.20 216 0.084 197 0.11 217 0.058 198 0.044 218 0.033 1990.11 219 0.13 200 0.10 220 0.073 201 0.14 221 0.058 202 0.095 222 0.041203 0.063 223 0.21 204 0.16 225 0.014 205 0.077 227 0.045 206 0.05 2280.18

[2139] TABLE 182 HCV polymerase HCV polymerase Ex. inhibitory activityEx. inhibitory activity No. IC₅₀ [μM] No. IC₅₀ [μM] 229 0.022 257 0.074230 0.17 259 0.10 231 0.073 260 0.27 232 0.015 262 0.013 233 0.028 2630.035 234 0.022 264 <0.01 235 0.036 265 0.014 236 0.075 266 0.018 2370.015 267 0.014 238 0.19 268 0.012 239 0.17 269 0.013 240 0.055 2700.012 248 0.012 271 0.024 249 0.022 272 0.066 250 0.018 273 0.041 2520.32 276 0.023 253 0.65 279 0.017 254 0.038 280 0.016 255 0.038 2810.052 256 0.079 282 0.019

[2140] TABLE 183 HCV polymerase HCV polymerase Ex. inhibitory activityEx. inhibitory activity No. IC₅₀ [μM] No. IC₅₀ [μM] 283 0.014 300 0.045284 0.014 301 0.017 285 0.012 303 0.10 286 0.014 304 0.017 287 0.012 3050.01 288 0.013 306 0.013 289 <0.01 307 0.022 290 0.012 308 0.023 2910.016 311 0.16 292 0.015 312 0.023 293 0.034 313 0.025 294 0.032 3140.097 295 0.045 315 0.028 296 0.034 316 0.022 297 0.022 317 0.032 2980.011 318 0.012 299 0.018 319 0.030

[2141] TABLE 184 HCV polymerase HCV polymerase Ex. inhibitory activityEx. inhibitory activity No. IC₅₀ [μM] No. IC₅₀ [μM] 320 0.036 328 0.015321 0.015 329 0.047 322 0.016 330 0.011 323 0.018 331 0.017 324 0.027332 0.023 325 0.019 333 0.016 326 0.018 334 0.016 327 0.019 335 0.013

[2142] TABLE 185 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

249 MS 672 (M + 1) 300 MHz, DMSO-d6 8.02(1H, d, J=1.5Hz), 8.11 (1H, d,J=1.8Hz), 7.96-7.81 (3H, m), 7.67(1H, s), 7.61-7.49(6H, m), 7.08(2H, d,J=8.6 Hz), 5.19(2H, s), 4.25(1H, m), 2.38-2.17(2H, m), 1.96-1.78(4H, m),1.70- #1.56(1H, m), 1.46-1.16(3H, m), 1.11(9H, s)

250 MS 616 (M + 1) 300 MHz, DMSO-d6 8.25(1H, d, J=1.5Hz), 8.16-8.08(2H,m), 7.99-7.38(2H, m), 7.66(2H, d, J=8.6Hz), 7.60-7.48(5H, m), 7.19(2H,d, J=8.6Hz), 5.17(2H, s), 4.31 (1H, m), 2.39-2.20(2H, m), 2.04-1.79(4H,m), 1.72-1.60 (1H, m), 1.50-1.18(3H, m)

251 MS 433 (M + 1) 300 MHz, DMSO-d6 cis and trans mixture 8.13 and8.11(total 1H, each s), 7.90-7.74(2H, m), 7.42-7.22(5H, m), 4.56 and4.52 (total 2H, each s), 4.42(1H, brs), 3.78-3.06 (2H, m) 2.33-1.33(18H,m)

[2143] TABLE 186 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

252 MS 509 (M + 1) 300 MHz, DMSO-d6 8.20(1H, d, J=1.5Hz), 7.96 (1H, d,J=8.6Hz), 7.84(1H, dd, J=8.6, 1.5Hz), 7.54(2H, d, J=6.9Hz),7.48-7.26(8H, m) 7.09(1H, t, J=7.3Hz), 5.43 (2H, s), 4.06(1H, m),2.40-2.20(2H, m), 2.01-1.83(4H, m), #1.75-1.64(1H, m), 1.51-1.28(3H, m)

253 MS 493 (M + 1) 300 MHz, DMSO-d6 8.21(1H, d, J=1.5Hz)7.93 (1H, d,J=8.7Hz), 7.85(1H, dd, J=8.4, 1.5Hz), 7.54-7.47 (2H, m), 7.40-7.24(6H,m), 7.15(1H, d, J=3.6Hz)) 7.11-7.05(1H, m), 6.81(1H, d, J=3.6 Hz),5.26(2H, s), 4.96 (1H, m), 2.32-2.13(2H, m), 1.95-1.72(4H, m), 1.68-1.55(1H, m), 1.43-1.18(3H, m)

254 MS 558 (M + 1) 300 MHz, DMSO-d6 8.25(1H, s), 8.02(1H, d, J=8.7Hz),7.90 (1H, dd, J=8.4, 1.4Hz), 7.80-7.71(2H, m), 7.67(2H, d, J=8.7Hz),7.33(2H, t, J=8.7Hz), 7.26(2H, d, J=8.7Hz), 5.46(2H, s) , 4.78 (2H, s),4.31(1H, m), 2.39-2.19(2H, m), 2.03-1.79(4H, m), #1.71-1.59(1H, m),1.50-1.17(3H, m)

[2144] TABLE 187 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

255 MS 568 (M + 1) 300 MHz, DMSO-d6 8.34(1H, s), 8.32(1H, d, J=8.8Hz),8.09-8.03(3H, m), 7.83 (2H, d, J=8.3Hz), 7.79(2H, d, J=8.8Hz), 7.36(2H,d, J=8.8Hz), 5.54(2H, s), 4.38 (1H, m), 2.74(3H, s), 2.40-2.18 (2H, m),2.13-1.96(2H, m), 1.93-1.78(2H, m), 1.73-1.57 (1H, m), 1.55-1.15(3H, m)

256 MS 585 (M + 1) 300 MHz, DMSO-d6 12.67(1H, brs), 8.23(1H, s) 7.94 and7.87(2H, ABq, J=8.6Hz), 7.79(1H, dd, J=8.7, 5.4Hz), 7.62-7.41(7H, m),6.80 (1H, dd, J=11.9, 2.3Hz), 6.69(1H, dd, J=8.1, 2.1Hz), 5.20(2H, s),3.93(1H, brt, J=15.3Hz), 2.30-2.11(2H, brm) 1.88-1.74(4H, brm),1.64-1.58(1H, brm), 1.41-1.14(3H, brm)

257 MS 603 (M + 1) 300 MHz, DMSO-d6 8.19(1H, d, J=8.7Hz) 7.93 (1H, s),7.83-7.71(3H, m), 7.50-7.39(4H, m), 7.34-7.10 (4H, m), 7.06(1H, dd,J=8.4, 2.9Hz), 5.09(2H, s), 4.34(1H, m), 3.82(3H, s), 2.39-2.19 (2H, m),2.11-1.98(2H, m), 1.94-1.79(2H, m), 1.74-1.58 (1H, m), 1.52-1.21 (3H, m)

[2145] TABLE 188 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

258 MS 567 (M + 1) 300 MHz, DMSO-d6 7.79 (1H, d, J = 6. 7 Hz), 7.56 (1H, d, J = 7. 5 Hz), 7.49 (2H, d, J = 8. 6 Hz), 7.42 (4H, s), 7.32 -7.23(3H, m), 7.09-7.03 (3H , m), 5.02 (2H, s), 4.46 (1H, m ), 3.82 (3H, s),1.95-1.83 (2 H, m), 1.75- # 1.44 (5H, m), 1.3 0-1.10 (2H, m), 0.89-0.71(1 H, m)

259 MS 591 (M + 1) 300 MHz, DMSO-d6 8.93 (2H, d, J = 6. 6 Hz), 8.36 (1H, s), 8.28 (1H, d, J = 8. 7 Hz) , 8.10-8.03 (3H, m), 7.85 (2H , d, J =8. 7 Hz), 7.33 (2H, d, J =8. 7 Hz), 7.23 (1H, s), 7.23 (1 H, s), 6.81(1H, s), 5.56 (2H, s), 4.39 (1H, m), 2.97, 2.92 ( # 6H, s), 2.40-2.18(2H, m), 2. 16-1.95 (2H, m), 1.90-1.75 ( 2H, m), 1.70-1.55 (1H, m), 1.50-1.15 (3H, m)

260 MS 564 (M + 1) 300 MHz, DMSO-d6 8.93 (2H, d, J = 6. 3 Hz) 8.35 ( 1H,s), 8.26 (1H, d, J = 8. 7 Hz) , 8.09-8.02 (3H, m), 7.86 (2H , d, J = 8.7 Hz), 7.50 (1H, s), 7 .35 (2H, d, J = 8. 4 Hz), 7.24 (2 H, d, J = 7. 8Hz), 5.60 (2H, s), # 4.39 (1H, m), 2.50-2.18 (2H, m), 2.15-1.95 (2H, m),1.90-1.75 (2H, m), 1.70-1.55 (1H, m) 1.50-1.10 (3H, m)

[2146] TABLE 189 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

261 MS 567 (M + 1) 300 MHz, DMSO-d6 8.22 (1H, d, J = 7. 8 Hz), 7.85 (1H, d, J = 6. 7 Hz), 7.63 (2H, d, J = 9. 0H), 7.51-7.38 (5H, m), 7.29(1H, d, J = 8. 3 Hz), 7.23 ( 1H, d, J = 3. 0 Hz), 7.06 (2H, d, J = 9. 0Hz), 7.06 (1H, dd, J = 8. # 6, 3. 0 Hz), 5.05 (2H, s), 4.41 -4.25 (1H,m), 3.83 (3H, s), 2 .40-2.20 (2H, m), 2.03-1.78 (4H, m), 1.72-1.57 (1H,m), 1 .50-1.18 (3H, m)

262 MS 580 (M + 1) 300 MHz, DMSO-d6 8.29 (1H, d, J = 1. 5 Hz), 8.26 (1H, d, J = 9. 0 Hz), 8.19 (1H, d, J = 1. 8 Hz), 8.13 (1H, brs), 8.08-7.96 (2H, m), 7.73 (2H, d, J = 9. 0 Hz), 7.57-7.43 (6H, m) , 7.24(2H, d, J = 9. 0 Hz), 5.14 (2H, s), 4.36 (1H, m) 2.38-2 # .18 (2H, m),2.12-1.97 (2H, m ), 1.93-1.80 (2H, m), 1.73-1 .58 (1H, m), 1.52-1.20(3H, m )

263 MS 548 (M + 1) 300 MHz, DMSO-d6 12.85 (1H, brs), 8.72 (1H, d, J = 4.8 Hz), 8.22 (1H, s), 8.14 (1H, d, J = 6. 3 Hz), 8.03and7. 76 (4H, ABq, J= 8. 6 Hz), 7.93a nd7.85 (2H, A′ B′ q, J = 8. 6 Hz) , 7.60and7.15 (4H,A″B″q, J =8. 7 Hz), 7.55 (1H, dd, J = 6. 3, # 4. 8 Hz), 5.19 (2H, s),4.26 (1 H, brt, J = 12. 6 Hz), 2.35-2.1 8 (2H, brm), 1.95-1.77 (4H, brm), 1.70-1.60 (1H, brm), 1. 45-1.15 (3H, brm)

[2147] TABLE 190 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

264 MS 586, 588 (M + 1) 300 MHz, DMSO-d6 8.23 (1H, d, J = 1. 0 Hz), 7.92( 1H, dd, J = 8. 7, 1. 0 Hz), 7.87 ( 1H, d, J = 8. 7 Hz), 7.60 (2H, d, J= 8. 6 Hz), 7.47 (2H, d, J = 8. 7 Hz), 7.44 (2H, d, J = 8. 7 Hz), 7 .30(1H, d, J = 8. 3 Hz), 7.23 (1 # H, d, J = 2. 6 Hz), 7.11 (2H, d, J =8. 7Hz), 7.06 (1H, dd, J = 8. 7 , 2. 6 Hz), 5.04 (2H, s), 4.36 ( 1H, m),3.83 (3H, s), 2.80-2. 70 (4H, m), 2.60-2.40 (2H, m) 2.30-2.20 (2H, m)

265 MS 608 (M + 1) 300 MHz, DMS-d6 8.30 (1H, d, J = 1. 5 Hz), 8.25 ( 1H,d, J = 9. 1 Hz), 8.03 (1H, dd , J = 8. 7, 1. 5 Hz), 7.76-7.96 ( 3H, m),7.55-7.49 (5H, m), 7. 42 (1H, d, J = 7. 6 Hz), 7.23 (2H , d, J = 8. 7Hz), 5.15 (2H, s), 4 .35 (1H, m), 3.01 (3H, # s), 2.9 7 (3H, s),2.37-2.20 (2H, m), 2.09-1.97 (2H, m), 1.94-1.8 1 (2H, m), 1.72-1.60 (1H,m), 1.50-1.21 (3H, m)

266 MS 642 (M + 1) 300 MHz, DMSO-d6 8.27 (1H, d, J = 1.5 Hz), 8.20 ( 1H,d, J = 9. 0 Hz), 8.00 (1H, dd , J = 8. 6, 1. 5 Hz), 7.82 (2H, d, J = 8.2 Hz), 7.76-7.65 (5H, m) , 7.56 (1H, dd, J = 7. 9, 1. 8 Hz) , 7.47 (1H,d, J = 7. 5 Hz), 7.20 (2H, d, J = 8. 6 Hz), 5.16 (2H, s # ), 4.32 (1H,m), 3.02 (3H, s), 2.98 (3H, s), 2.38-2.19 (2H, m), 2.07-1.95 (2H, m),1.93-1.80 (2H, m), 1.72-1.58 (1H, m), 1.52-1.18 (3H, m)

[2148] TABLE 191 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

267 MS 620 (M + 1) 300 MHz, DMSO-d6 8.34 (2H, m), 8.03 (1H, d, J = 8 . 3Hz), 7.77-7.68 (3H, m), 7. 54-7.40 (4H, m), 7.33 (2H, d, J = 8. 6 Hz),7.24 (2H, d, J = 9. 0 Hz), 5.16 (2H, s), 4.36 (1H, m ), 3.01 (3H, s),2.97 (3H, s), 2.40-2.20 (2H, m), 2.11-1.9 # 7 (2H, m), 1.93-1.81 (2H,m), 1.71-1.60 (1H, m). 1.50-1.2 1 (3H, m)

268 MS 612 (M + 1) 300 MHz, DMSO-d6 8.67-8.59 (1H, m), 8.30 (1H, s),8.13-8.20 (2H, m), 8.02-7.92 (2H, m), 7.65 (1H, t, J = 8 .3 Hz),7.56-7.45 (5H, m), 7. 18 (1H, dd, J = 12. 0, 2. 2 Hz), 7 .05 (1H, dd, J= 8. 6, 2. 2 Hz), 5 .14 (2H, s), 4.09 (1H, m), 2.8 # 2 (3H, d, J = 4. 5Hz), 2.84-2.1 2 (2H, m), 1.99-1.79 (4H, m), 1.71-1.59 (1H, m), 1.49-1.21 (3H, m)

269 MS 626 (M + 1) 300 MHz, DMSO-d6 8.29 (1H, s), 8.13 (1H, d, J = 9 . 0Hz), 7.97 (1H, dd, J = 8. 6, 1 . 5 Hz), 7.71 (1H, d, J = 1. 8 Hz) , 7.63(1H, t, J = 8. 2 Hz), 7.56 -7.41 (6H, m), 7.17 (1H, dd, J =12. 0, 2. 2Hz), 7.03 (1H, dd, J = 8. 2, 1. # 8 Hz), 5.14 (2H, s), 4.15-4.00 (1H,m), 3.01 (3H, s), 2.98 (3H, s), 2.32-2.13 ( 2H, m) 1.95-1.79 (4H, m),1.7 2-1.59 (1H, m), 1.45-1.21 (3 H, m)

[2149] TABLE 192 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

270 MS 598 (M + 1) 300 MHz, DMSO-d6 8.24 (1H, d, J = 1. 4 Hz), 8.19 (1H, d, J = 1. 8 Hz), 8.11 (1H, br s), 8.02-7.85 (3H, m), 7.60-7.44 (7H,m), 7.10 (1H, dd, J =12. 0, 2. 1 Hz), 6.98 (1H, dd, J =8. 4, 2. 1 Hz),5.11 (2H, s), 3 .98 (1H, m), 2.30-2.12 (2H, m # ), 1.91-1.73 (4H, m),1.71-1 .58 (1H, m), 1.45-1.15 (3H, m )

271 MS 652 (M + 1) 300 MHz, DMSO-d6 8.29 (1H, d, J = 1. 5 Hz), 8.24 (1H, d, J = 8. 7 Hz), 8.07-7.98 ( 3H, m), 7.80-7.68 (5H, m), 7. 56 (1H,dd, J = 8. 0, 1. 8 Hz), 7. 47 (1H, d, J = 8. 0 Hz), 7.21 (2H , d, J = 8.4 Hz), 5.18 (2H, s), 4 .34 (1H, m), # 3.27 (3H, s), 3.0 2 (3H, s), 2.98(3H, s), 2.38-2.18 (2H, m), 2.10-1.95 (2H, m), 1.93-1.79 (2H, m),1.72-1.59 (1H, m), 1.50-1.19 (3H, m)

272 MS (575 (M + 1) 300 MHz, DMSO-d6 8.97 (1H, d, J = 1. 8 Hz) 8.85 (1H, d, J = 4. 7 Hz), 8.46 (1H, d, J = 8. 0 Hz), 8.39-8.26 (2H, m) , 8.06(1H, d, J = 8. 7 Hz), 7.99 -7.64 (6H, m), 7.24 (2H, d, J =8. 7 Hz), 5.25(2H, s), 4.36 (1 H, m), 3.03 (3H, s), # 2.97 (3H, s), 2.39-2.19 (2H, m),2.14-1.96 (2H, m), 1.94-1.78 (2H, m), 1.73-1.60 (1H, m), 1.21-1.55 (3H,m)

[2150] TABLE 193 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

273 MS 645 (M + 1) 300 MHz, DMSO-d6 8.30 (1H, s), 8.27 (1H, d, J = 8 . 7Hz), 8.05 (1H, d, J = 8. 7 Hz) , 7.77-7.67 (3H, m), 7.58-7. 48 (6H, m),7.22 (2H, d, J = 8. 4 Hz), 5.18 (2H, s), 4.35 (1H, b rt, J = 9. 8 Hz),3.06-2.88 (12 H, brm), 2.38-2.20 (2H, brm) # , 2.08-1.96 (2H, brm),1.90-1.80 (2H, brm), 1.70-1.60 (1 H, brm), 1.49-1.22 (3H, brm)

274 MS 601 (M + 1) 300 MHz, DMSO-d6 mixture of cis and trans 8.35, 8.34(1H, s), 8.15-8.1 0 (2H, m), 7.79-7.70 (3H, m), 7.49 (2H, d, J = 8. 7Hz), 7.44 ( 2H, d, J = 8. 7 Hz), 7.31 (1H, d, J = 8. 4 Hz), 7.25-7.19(2H, m) , 7.07 (1H, d, # J = 8. 5 Hz), 5.08 (2H, s), 4.75 (1H, m), 3.83(3 H, s), 3.70-1.90 (8H, m)

275 MS 617 (M + 1) 300 MHz, DMSO-d6 8.33 (1H, s), 8.13 (1H, d, J = 7 . 5Hz), 7.93 (1H, d, J = 8. 8 Hz) , 7.74 (2H, d, J = 8. 7 Hz), 7.49 (2H, d,J = 8. 6 Hz), 7.44 (2H, d , J = 8. 6 Hz), 7.31 (1H, d, J = 8. 5 Hz),7.25-7.15 (3H, m), 7.0 # 7 (1H, d, J = 8. 5 Hz), 5.08 (2H, s), 4.98 (1H,m), 3.83 (3H, s) , 3.65-3.45 (2H, m), 3.30-3. 10 (2H, m), 3.00-2.75 (2H,m) , 2.60-2.30 (2H, m)

[2151] TABLE 194 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

276 MS 603 (M + 1) 300 MHz, DMSO-d6 8.25 (1H, s), 7.93and7.87 (2 H, ABq,J = 9. 1 Hz), 7.55 (1H, t , J = 8. 6 Hz), 7.48and7.42 (4H , A′ B′ q, J =8. 6 Hz), 7.31 (1H, d, J = 8. 5 Hz), 7.24 (1H, d, J = 2 , 6 Hz),7.09-6.95 (3H, m), 5. # 05 (2H, s), 4.11 (1H, brt, J = 1 4. 0 Hz), 3.84(3H, s), 2.83-2 .67 (4H, brm), 2.50-2.32 (2H , brm), 2.21-2.10 (2H, brm)

277 MS 619 (M + 1) 300 MHz, DMSO-d6 cis and trans mixture 8.28and8.24(total 1H, each s), 7.94-7.87 (1H, m), 7.60-7.41 (5H, m), 7.31 (1H, d, J= 8 . 5 Hz), 7.23-7.21 (1H, m), 7. 12-7.05 (2H, m), 7.00-6.95 ( 1H, m),5.06and5.05 (total # 2H, each s), 4.47and4.34 (total 1H, each brs), 3.83(3H, s), 3.12-1.7 6 (8H, m)

278 MS 635 (M + 1) 300 MHz, DMSO-d6 12.9 (1H, brs), 8.27 (1H, s),7.97and7.74 (2H, ABq, J = 8. 6 Hz), 7.58 (1H, t, J = 8. 6 Hz), 7.49and7.43 (4H, A′ B′ q, J = 8. 5 Hz), 7.31 (1H, d, J = 8. 5 Hz), 7.22(1H, d, J = 2. 6 Hz), 7.13- # 6.92 (3H, m), 5.05 (2H, s), 4. 67 (1H,brt, J = 14. 2 Hz), 3.57 -3.40 (2H, brm), 3.20-3.05 ( 2H, brm),2.91-2.70 (2H, brm , 2.28-2.11 (2H, brm)

[2152] TABLE 195 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

279 MS 644 (M + 1) 300 MHz, DMSO-d6 8.30 (1H, s), 8.23 (1H, d, J = 8 . 7Hz), 8.06-8.00 (2H, m), 7. 83 (1H, dd, J = 8. 0, 1. 8 Hz), 7. 71 (2H, d,J = 8. 4 Hz), 7.64 (1H , d, J = 8. 0 Hz), 7.59-7.54 (4H , m), 7.22 (2H,d, J = 8.4 Hz), 5 # .25 (2H, s), 4.33 (1H, m), 2.6 6 (3H, s), 2.66 (3H,s), 2.37-2.19 (2H, m), 1.93-1.80 (2H, m), 1.70-1.59 (1H, m,) 1.47-1.21(3H, m)

280 MS 615 (M + 1) 300 MHz, DMSO-d6 8.32-8.23 (3H, m), 8.08-8.0 1 (2H,m), 7.73 (2H, d, J = 8. 6 H z), 7.65 (1H, d, J = 8. 2 Hz), 7. 59-7.51(4H, m), 7.25 (2H, d, J = 8. 6 Hz), 5.21 (2H, s), 4.34 (1H, m), 3.32(3H, s), 2.37-2 .19 (2H, m), # 2.10-1.98 (2H, m ), 1.93-1.80 (2H, m),1.71-1 .60 (1H, m), 1.51-1.21 (3H, m )

281 MS 315 300 MHz, DMSO-d6 8.30 (1H, d, J = 1. 5 Hz), 8.24 ( 1H, s),8.14 (1H, d, J = 8. 6 Hz) , 8.07-7.95 (2H, m), 7.63 (1H , t, J = 8. 6Hz), 7.57-7.47 (5H m), 7.16 (1H, dd, J = 12. 0, 2. 2 Hz), 7.03 (1H, dd,J = 8. 6, 2. 2 Hz), 5.17 (2H, s), # 4.06 (1H, m), 3.90 (3H, s),2.31-2.11 ( 2H, m), 1.97-1.78 (4H, m), 1. 71-1.59 (1H, m), 1.43-1.22 (3H, m)

[2153] TABLE 196 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

282 MS 580 (M + 1) 300 MHz, DMSO-d6 8.36 (1H, s), 8.35 (1H, d, J = 9 . 3Hz), 8.09 (1H, d, J = 9. 3 Hz) , 7.78 (2H, d, J = 8. 7 Hz), 7.48 -7.25(9H, m), 5.09 (2H, s), 4 .39 (1H, m), 3.04 (6H, s) 2.4 0-2.15 (2H, m),2.10-1.95 (2 H, m), # 1.90-1.75 (2H, m), 1.7 0-1.55 (1H, m), 1.50-1.20(3 H, m)

283 MS 630 (M + 1) 300 MHz, DMSO-d6 10.03 (1H, s), 8.33 (1H, s), 8 .29(1H, d, J = 8. 7 Hz), 8.06 (1 H, d, J = 9. 0 Hz), 7.74 (2H, d, J =9. 0Hz), 7.51-7.42 (5H, m), 7.37-7.30 (2H, m), 7.22 (2H, d, J = 8. 7 Hz),5.10 (2H, s), 4. 37 # (1H, m), 3.06 (3H, m), 2.40 -2.18 (2H, m),2.15-1.95 (2H m), 1.90-1.80 (2H, m), 1.75 -1.55 (1H, m), 1.50-1.20 (3H ,m)

284 MS 654 (M + 1) 300 MHz, DMSO-d6 8.30 (1H, s), 8.14 (1H, d, J = 8 . 7Hz), 7.97 (1H, d, J = 8. 7 Hz) , 7.96-7.41 (8H, m), 7.16 (1H , dd, J =12. 4, 2. 2 Hz), 7.03 (1 H, dd, J = 8. 4, 2. 2 Hz), 5.15 (2 H, s), 4.15(1H, m), 3.54-3.1 # 6 (4H, m), 2.33-2.13 (2H, m), 1.97-1.79 (4H, m),1.70-1.0 2 (9H, m)

[2154] TABLE 197 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

285 MS 640 (M + 1) 300 MHz, DMSO-d6 8.37 (1H, d, J = 7. 3 Hz), 8.30 (1H, s), 8.19-8.12 (2H, m), 8. 02-7.95 (2H, m), 7.65 (1H, t, J = 8. 4Hz), 7.56-7.43 (5H, m) , 7.18 (1H, dd, J = 12. 0, 1. 8 Hz ), 7.06 (1H,dd, J = 8. 4, 2. 1 Hz # ), 5.13 (2H, s), 4.22-4.03 (2 H, m), 2.34-2.13(2H, m), 1.9 9-1.78 (4H, m), 1.72-1.57 (1 H, m), 1.44-1.14 (3H, m), 1.20, 1.18 (6H, each s)

286 MS 666 (M + 1) 300 MHz, DMSO-d6 8.29 (1H, s), 8.13 (1H, d, J = 8 . 7Hz), 7.97 (1H, dd, J = 8, 7, 1 . 4 Hz), 7.69-7.40 (8H, m), 7. 16 (1H,dd, J = 12. 0, 2. 2 Hz), 7 .02 (1H, dd, J = 8. 4, 2. 2 Hz), 5 .15 (2H,s), 4.07 (1H, m), 3.7 # 1-3.23 (2H, m), 1.98-1.71 (4 H, m), 1.71-1.18(10H, m)

287 MS 652 (M + 1) 300 MHz, DMSO-d6 8.29 (1H, s), 8.13 (1H, d, J = 8 . 0Hz), 7.97 (1H, d, J = 8. 4 Hz) , 7.83 (1H, s), 7.68-7.41 (7H , m), 7.17(1H, d, J = 12. 0 Hz), 7.03 (1H, d, J = 8. 4 Hz), 5.15 ( 2H, s), 4.07(1H, m), 3.58-3. # 41 (4H, m) 2.34-2.13 (2H, m) , 1.97-1.77 (8H, m),1.71-1. 58 (1H, m), 1.49-1.18 (3H, m)

[2155] TABLE 198 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

288 MS 642 (M + 1) 300 MHz, DMSO-d6 8.62(1N, m), 8.31(1H, s),8.22-8.14(2H, m), 8.99(2H, d, J=8.7Hz), 7.66(1H, t, J=7.7Hz),7.58-7.44(5H, m), 7.19 (1H, dd, J=8.7, 2.2Hz), 5.14 (2H, s), 4.11(1H,m), 3.67-3.49(2H, m), 3.45-3.30(2H, m), 2.37-2.12(2H, m), 2.00-1.76(4H,m), 1.70-1.58(1H, m), 1.48-1.17(3H, m)

289 MS 682 (M + 1) 400 MHz, DMSO-d6 8.28(1H, s), 8.11(1H, d, J=8.9Hz),7.96(1H, d, J=8.9Hz), 7.68(1H, s), 7.62(1H, t, J=8.2Hz), 7.55-7.41(6H,m), 7.15(1H, d, J=11.7Hz), 7.02(1H, d, J=8.4Hz), 5.14(2H, s),4.12-3.13(6H, m), 2.30-1.19(13H, m)

290 MS 668 (M + 1) 400 MHz, DMSO-d6 8.29(1H, s), 8.15(1H, d, J=8.6Hz),7.98(1H, d, J=8.8Hz), 7.72(1H, s), 7.64(1H, t, J=8.8Hz), 7.57-7.43(6H,m), 7.18(1H, dd, J=12.1, 2.1Hz), 7.03(1H, d, J=10.7Hz), 5.12(2H, s),4.15‥4.01(1H, m), 3.75-3.33(8H, m), 2.31-2.14(2H, m), 1.96-1.78(1H, m),1.70-1.58(1H, m), 1.47-1.21(3H, m)

[2156] TABLE 199 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

291 MS 684 (M + 1) 400 MHz, DMSO-d6 8.29(1H, s), 8.14(1H, d, J=8.9Hz),7.97(1H, d, J=8.6Hz), 7.71 (1H, s), 7.63(1H, t, J=8.2Hz), 7.56-7.42(6H,m), 7.17(1H, d, J=12.3Hz), 7.03 (1H, d, J=10.7Hz), 5.14(2H, s), 4.07(1H,m), 3.96-3.52(4H, m), 2.79-2.56(4H, m), 2.32-2.14(2H, m), 1.97-1.79(4H,m), 1.71-1.58(1H, m), 1.51-1.19(3H, m)

292 MS 656 (M + 1) 300 MHz, DMSO-d6 9.07-8.99(1H, m), 8.30(1H, s),8.23-8.12(2H, m), 8.04-7.95(2H, m), 7.65(1H, t, J=8.2Hz), 7.60-7.45(5H,m), 7.19(1H, dd, J=12.0, 2.6Hz), 7.06(1H, dd, J=8.6, 2.2Hz), 5.16(2H,s), 4.18-4.02(1H, m), 3.97(2H, d, J=6.0Hz), 2.33-2.14(2H, m),1.99-1.79(4H, m), 1.72-1.59(1H, m), 1.45-1.19(3H, m)

293 MS 637 (M + 1) 300 MHz, DMSO-d6:8.21(1H, s), 7.94and7.86(2H, ABq,J=8.6Hz), 7.72(1H, d, J=2.4Hz), 7.59and7.11 (4H, A′B′q, J=8.9Hz),7.53(1H, dd, J=8.4, 2.4Hz), 7.38(1H, d, J=8.4Hz), 7.36and7.32(4H, A″B″q,J=8.1Hz), 5.07(2H, s), 4.27(1H, brt, J=13.8Hz), 2.87 (2H, t, J=7.8Hz),2.57(2H, t, J=7.8Hz), 2.35-2.20(2H, brm), 1.96-1.79(4H, brm),1.68-1.59(1H, brm), 1.47-1.18(3H,brm)

[2157] TABLE 200 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

294 MS 567 (M + 1) 300 MHz, DMSO-d6 8.30(1H, s), 8.25and8.03 (2H, ABq,J=8.9Hz), 7.73(1H, s), 7.73(2H, d, J=8.6Hz), 7.55 (1H, dd, J=8.0,2.3Hz), 7.40 (4H, s), 7.39(1H, d, J=8.0Hz), 7.23(2H, d, J=8.6Hz), 5.11#(2H, s), 4.55(2H, s), 4.36 (1H, brt, J=14.8Hz), 2.37-2.19 (2H, brm),2.09-1.96(2H, brm), 1.91-1.79(2H, brm), 1.71-1.59(1H, brm),1.50-1.20(3H, brm)

295 MS 581 (M + 1) 300 MHz, DMSO-d6 8.30(1H, s), 8.25and8.04(2H, ABq,J=8.7Hz), 7.74(1H, s), 7.72 (2H, d, J=8.7Hz), 7.56(1H, d, J=8.7Hz),7.48-7.35 (5H, m), 7.22(2H, d, J=8.7Hz), 5.11(2H, s), 4.46(2H, s),#4.35(1H, brt, J=14.8Hz), 3.31(3H, s), 2.37-2.17(2H, brm), 2.07-1.95(2H,brm), 1.92-1.79(2H, brm), 1.73-1.56 (1H, brm), 1.52-1.20(3H, brm)

296 MS 581 (M + 1) 300 MHz, DMSO-d6 8.21(1H, d, J=1.5Hz), 7.98 (1H, d,J=1.2Hz), 7.97-7.91 (2H, m), 7.84(1H, dd, J=8.7, 1.5Hz), 7.77(1H, d,J=2.1Hz), 7.70(1H, d, J=7.5Hz), 7.60-7.54(4H, m), 7.43(1H, d, J=#8.4Hz), 7.09(2H, d, J=8.7Hz), 5.05(2H, s), 4.25(1H, brt, J=14.8Hz),2.36-2.18 (2H, brm), 1.95-1.79(4H, brm), 1.71-1.6 (1H, brm),1.43-1.18(3H, brm)

[2158] TABLE 201 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

297 MS 583 (M + ) 300 MHz, DMSO-d6 12.7(1H, brs), 8.21(1H, s),7.94and7.85(2H, ABq, J=8.6Hz), 7.60-7.55(3H, m), 7.49 and7.45(4H, A′B′q,J=8.3Hz), 7.12(2H, d, J=8.7Hz), 5.05(2H, s), 4.26 #(1H, brt, J=13.0Hz),2.54(3H, s), 2.38-2.20 (2H, brm), 1.97-1.80(4H, brm), 1.71-1.59(1H,brm), 1.47-1.20(3H, brm)

298 MS 599 (M + 1) 300 MHz, DMSO-d6 8.22(1H, s), 8.01(1H, s),7.95and7.86(2H, ABq, J=8.6Hz), 7.79(1H, d, J=7.8Hz), 7.58 (3H, t,J=7.5Hz), 7.53(4H, s), 7.13(2H, d, 8.7Hz), 5.15(2H, s), 4.26 #(1H, brt,J=13.8Hz), 2.83(3H, s), 2.37-2.18(2H, brm), 1.95-1.78(4H, brm),1.70-1.59(1H, brm), 1.47-1.17(3H, brm)

299 MS 562 (M + 1) 300 MHz, DMSO-d6 8.43-8.16(3H, m), 8.07-7.94 (2H, m),7.72(2H, d, J=8.6Hz), 7.62-7.49 (5H, m), 7.23(2H, d, J=8.6Hz), 5.16 (2H,s), 4.34(1H, m), 2.39-2.20(2H, m), #2.10-1.96(2H, m), 1.93-1.80(2H, m),1.71-1.58(1H, m), 1.49-1.19(3H, m)

[2159] TABLE 202 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

300 MS 523 (M + 1) 300 MHz, DMSO-d6:2.77(1H, brs), 8.83(2H, d, J=1.9Hz),8.56 (2H, dd, J=4.9, 1.9Hz), 8.22(1H, d, J=1.5Hz), 7.97(2H, dt, J=7.9,1.9Hz), 7.95(1H, d, J=8.6Hz), 7.87(1H, dd, # J=8.6, 1.5Hz), 7.57(1H, t,J=8.7Hz), 7.46(2H, dd, J=7.9, 4.9Hz), 7.26(1H, dd, J=12.0, 4.9Hz),7.14(1H, dd, J=8.8, 2.3Hz), 6.99(2H, s), 3.94 (1H, brt), 2.26-2.09 (2H,m), 1.87-1.73(4H, m), 1.67-1.57 (1H, m) 1.42-1.13(3H, m)

301 MS 663 (M + 1) 300 MHz, DMSO-d6 8.22(1H, s), 7.95(1H, d, J=8.7Hz),7.87(1H, dd, J=1.5Hz, 9.0Hz), 7.62(4H, d, J=8.4Hz), 7.55(1H, t,J=9.0Hz), 7.44(4H, d, J=8.1Hz), 7.20(1H, # dd, J=2.1Hz, 12.0Hz), 7.11(1H, dd, J=2.1Hz, 8.7Hz), 6.86 (1H, s), 3.94 (1H, m), 2.96, 2.88(12H,s), 2.35-2.00(2H, m), 1.95-1.70 (4H, m), 1.65-1.50(1H, m), 1.45-1.10(3H,m)

302 MS 532 (M + 1) 300 MHz, DMSO-d6 8.14(1H, s), 7.88(1H, d, J=8.4Hz),7.68(1H, d, J=8.7Hz), 7.64-7.55(3H, m), 7.50(1H, t, J=8.7Hz),7.22-7.17(3H, m), 7.11(1H, s), 7.08-7.00(2H, m), 3.90(1H, m),2.15-2.00(2H, m), 1.95-1.50(5H, m), 1.45-1.00(3H, m)

[2160] TABLE 203 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

303 MS 640 (M + 1) 300 MHz, CDCl3 8.49(1H, s), 7.98(1H, dd, J=8.6,1.5Hz), 7.71(1H, d, J=1.8Hz), 7.66(1H, d, J=8.6Hz), 7.55-7.29(7H, m),6.80(1H, dd, J=8.2, 2.2Hz), 6.69(1H, dd, J=11.2, 2.2Hz), 4.99(2H, s),4.10-3.92(1H, m), 3.95(3H, s), 3.15(3H, s), 3.06(3H, s), 2.31-2.14(2H,m), 2.04-1.86(4H, m), 1.81-1.71(1H, m), 1.41-1.21(3H, m)

304 MS 608 (M + 1) 300 MHz, DMSO-d6 8.21(1H, s), 7.94(1H, d, J=8.7Hz),7.84(1H, d, J=9.1Hz), 7.70 (1H, s), 7.26-7.39(9H, m), 7.11(2H, d,J=8.4Hz), 5.11(2H, s), 4.26(1H, m), 3.01(3H, s), 2.97(3H, s),2.38-2.19(2H, m), 1.97-1.78(4H, m), 1.72-1.57(1H, m), 1.48-1.17(3H, m)

305 MS 599 (M + 1) 300 MHz, DMSO-d6 8.24(2H, s), 8.03(1H, d, J=8.0Hz),7.96(1H, d, J=8.8Hz), 7.87(1H, d, J=9.1Hz), 7.60-7.46(6H, m), 7.09(1H,dd, J=12.0, 1.8Hz), 6.97(1H, dd, J=8.4, 1.8Hz), 5.16(2H, s), 3.97 (1H,m), 2.31-2.11(2H, m), 1.92-1.73(4H, m) 1.701.57(1H, m), 1.46-1.13(3H, m)

[2161] TABLE 204 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

306 MS 577 (M + 1) 300 MHz, DMSO-d6 12.84(1H, brs), 8.21(1H, s),7.98-7.84(5H, m), 7.58(2H, d, J=8.7Hz), 7.54(2H, d, J=7.8Hz), 7.34(1H,d, J=8.7Hz), 7.26(1H, d, J=2.4Hz), 7.13-7.06(3H, m), 5.06(2H, s),4.26(1H, brt, J=12.7Hz), 3.84(3H, s), 2.36-2.17(2H, brm), 1.99-1.80(4H,brm), 1.73-1.59(1H, brm), 1.47-1.17(3H, brm)

307 MS 617 (M + 1) 300 MHz, DMSO-d6 8.22(1H, s), 8.04(1H, s), 7.96(2H,d, J=8.1Hz), 7.87(2H, s), 7.72(1H, d, J=1.2Hz), 7.59-7.41(7H, m),5.12(2H, s), 4.25(1H, brt, J=11.8Hz),3.02(3H, brs), 2.98(3H, brs),2.38-2.15(2H, brm), 1.93-1.76(4H, brm), 1.71-1.59 (1H, brm),1.46-1.16(3H, brm)

308 MS 552 (M + 1) 300 MHz, DMSO-d6 8.27(1H, s), 8.08(1H, d, J=9.0Hz),7.93 (1H, d, J=8.7Hz), 7.65(2H, d, J=8.7Hz), 7.46 (2H, d, J=8.1Hz),7.42(2H, d, J=8.4Hz), 7.30-7.04(5H, m), 5.03(2H, s), 4.32 (1H, m),2.40-2.10(2H, m), 2.05-1.10 (8H, m)

[2162] TABLE 205 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

309 MS 300 MHz, DMSO-d6 8.33(1H, s), 8.15and7.99(2H, ABq, J=8.9Hz),7.34and7.59 (4H, A′B′q, J=8.3Hz), 7.46(2H, d, J=8.4Hz), 7.22-7.16(3H,m), 7.01-6.98(2H, m), 4.27and4.23(2H, A″B″q, J=12.9Hz), 3.78 (3H, s),2.39-2.21(2H, brm), 2.07-1.95(2H, brm), 1.91-1.80(2H, brm),1.72-1.59(1H, brm), 1.49-1.17(3H, brm)

310 MS 615 (M + 1) 300 MHz, DMSO-d6 8.33(1H, s), 8.09and7.95 (2H, ABq,J=8.7Hz), 7.87and7.71(4H, A′B′q, J=8.0Hz), 7.43(2H, d, J=7.8Hz),7.15(1H, d, J=8.7Hz), 7.07-7.02(4H, m), 4.66(2H, s), 4.23(1H, brt,J=11.8Hz), 3.76(3H, s), 2.38-2.20 (2H, brm), 2.04-1.93(2H, brm),1.89-1.79(2H, brm), 1.70-1.59(1H, brm), 1.49-1.18(3H, brm)

311 MS 583 (M + 1) 300 MHz, DMSO-d6 8.30(1H, s), 8.21and8.01(2H, ABq,J=8.7Hz), 7.65(2H, d, J=8.4Hz), 7.52-7.41 (6H, m), 7.20(1H, d, J=8.4Hz),7.14 (1H, d, J=2.7Hz), 6.97(1H, dd, J=8.4, 2.4Hz), 4.31(1H, brt,J=9.8Hz), 4.28(2H, s), 3.78(3H, s), 2.37-2.20(2H, brm), 2.07-1.95(2H,brm), 1.92-1.80(2H, brm), 1.71-1.60(1H, brm), 1.50-1.19(3H, brm)

[2163] TABLE 206 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

312 MS 609 (M + 1) 300 MHz, DMSO-d6 8.22(1H, s), 8.12(1H, d, J=8.4Hz),8.00-7.84(5H, m), 7.70(4H, d, J=8.4Hz), 7.56(1H, t, J=8.6Hz), 7.23(1H,d, J=12.0Hz), 7.13(1H, d, J=8.6Hz), 6.97 (1H, s), 3.92(1H, m),2.35-2.00(2H, m), 1.95-1.70(4H, m), 1.65-1.55(1H, m), 1.50-1.05(3H, m)

313 MS 522 (M + 1) 300 MHz, DMSO-d6 8.89(1H, brs), 8.63(1H, brs),8.24(1H, s), 8.11(1H, d, J=7.8Hz), 7.99(1H, d, J=8.8Hz), 7.89(1H, d,J=9.9Hz), 7.61-7.55(4H, m), 7.43(2H, t, J=7.7Hz), 7.34(1H, t, J=7.2Hz),7.24(1H, d, J=12.0Hz), 7.14(1H, d, J=8.6Hz), 6.95(1H, s), 3.96(1H, m),2.35-2.05(2H, m), 2.00-1.50(5H, m), 1.45-1.10(3H, m)

314 MS 626 (M + 1) 300 MHz, CDCl3 8.48(1H, d, J=1.4Hz), 8.05(1H, d,J=1.8Hz), 8.98(1H, d, J=8.6Hz), 7.82(1H, d, J=7.9Hz), 7.66(1H, d,J=8.6Hz), 7.55-7.24(6H, m), 6.78(1H, dd, J=8.6, 2.6Hz), #6.69(1H, dd,J=11.6Hz), 2.2Hz), 6.40-6.30(1H, m), 4.99(2H, s), 4.02(1H, m), 3.95(3H,s), 3.05(3H, d, J=4.8Hz), 2.32-2.13 (2H, m), 2.03-1.87(4H, m),1.81-1.71(1H, m), 1.46-1.23(3H, m)

[2164] TABLE 207 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

503 MS 412 (M + 1) 300 MHz, DMSO-d6 8.23(1H, s), 7.76(1H, d, J=8.7Hz),7.58(1H, d, J=3.8Hz), 7.51-7.32(7H, m), 7.17 (2H, d, J=8.7Hz), 6.55(1H,s), 5.18 (2H, s), 4.75(1H, m), 2.35-2.12(2H, m), 2.10-1.85(4H, m),1.80-1.50(2H, m)

701 MS 568 (M + 1) 300 MHz, DMSO-d6 8.96(1H, s), 8.50(1H, s), 7.77 (2H,d, J=8.7Hz), 7.50-7.40(4H, m), 7.30 (1H, d, J=8.4Hz), 7.24(1H, d,J=2.4Hz), 7.16 (2H, d, J=8.4Hz), 7.06(1H, dd, J=2.4Hz, 8.1Hz), 5.06(2H,s), 4.31(1H, s), 3.83(3H, s), 2.80-2.55 (2H, m), 2.00-1.80(4H, m),1.70-1.55(1H, m), 1.40-1.15 (3H, m)

[2165] TABLE 208 >90% Example No. Purity (NMR) 1H NMR (δ) ppm

315 MS 538 (M + 1) 300 MHz, DMSO-d6 8.84 (2H, d, J = 6. 3 Hz), 8.28 (1H, s), 8.17and7.99 (2H, ABq, J = 8 .7 Hz), 7.87-7.85 (3H, m), 7.70 -7.50(3H, m), 7.52 (1H, d, J = 8. 3 Hz), 7.18 (2H, d, J = 8. 7 Hz), 5. 22(2H, s) 4.31 (1H, br t, # J = 12. 5 Hz), 2.38-2.18 (2H, m ), 2.03-1.78(4H, m), 1.70-1.5 8 (1H, m), 1.50-1.23 (3H, m)

316 MS 670 (M + 1) 300 MHz, DMSO-d6 9.23 (1H, t, J = 6. 3 Hz), 8. 29(1H, s), 8.25-8.22 (2H, m), 8.03 (2H, d, J = 7. 9 Hz), 7.55-7.48 (5H, m)7 .34 (4H, d, J = 4. 4 Hz), 7.28-7.22 (3H, m), 5.15 (2H, s), 4.52 (2H, d, J = 5. 9 Hz), 4.35 (1H, br # t, J = 12. 1 Hz), 2.37-2.18 (2H, m) ,2.08-1.95 (2H, m), 1.91-1.79 ( 2H, m), 1. 72-1.59 (1H, m), 1.47-1.19(3H, m)

317 MS 676 (M + 1) 300 MHz, DMSO-d6 8.59 (1H, t, J = 5. 5 Hz), 8. 8 (1H,s), 8.21and8.01 (2H, ABq, J = 8. 8 Hz), 8.16 (1H, s), 7.97and7.46 ( 2H,A′ B′ q, J = 8. 0 Hz), 7.71and7. 23 (4H, A″ B″ q, J = 8. 7 Hz), 1.53and7.49 (4H, A″ B″ q, J = 9.2 Hz), 5 # .14 (2H, s), 4.34 (1H, br t, J =12. 8 Hz), 3.14 (2H, t J = 6.3 Hz), 2.38-2.18 (2H, m), 2.07-1. 78 (4H.m), 1.78-1.47 (7H, m), 1. 47-1.07 (6H, m), 1.03-0.33 (2H, m)

[2166] TABLE 209 >90% Example No. Purity (NMR) 1H NMR (δ) ppm

318 MS 671 (M + 1) 300 MHz, DMSO-d6 9.63 (1H, t, J = 4. 8 Hz),8.86and1.97 ( 4H, ABq, J = 6. 6 Hz), 8.30 (1H, s), 8.27 (1H, s),8.23and8.03 (2H, A ′ B′ q, J = 8. 8 Hz), 8.09and7.54 (2 H, A″ B″ q, J =8. 1 Hz), 7.73and7.2 4 (4H, A″ B″ q, J = 8. 8 Hz), 7.54a # nd7.52 (4H,A″″ B″″ q, J = 8. 8 Hz), 5.16 (2H, s) 4.78 (2H, d, J = 5. 6 Hz ), 4.35(1H, br t, J = 11. 0 Hz), 2.39-2.19 (2H, m) , 2.07-1.96 (2H, m),1.91-1.78 ( 2H, m) 1.70-1.57 (1H, m) 1.50-1 .19 (3H, m)

319 MS 684 (M + 1) 300 MHz, DMSO-d6 8. 28 (1H, s), 8.24and8.03 (2H, ABq, J = 9. 0 Hz), 7.77 (1H, s), 7.70 (2H, d, J = 8. 4 Hz), 7.64-7.10 (13H, m), 5.16 (2H, s), 4.74and4.57 (total 2H, each br s), 4.34 (1H, br t,J = 11. 7 Hz), 2.90 (3H, s), 2.35 -2.17 (2H, m), 2.07-1.93 (2H, m) # ,1.93-1.78 (2H, m), 1.71-1.57 ( 1H, m), 1.51-1.19 (3H, m)

320 MS 575 (M + 1) 300 MHz, DMSO-d6 8.94and8.06 (4H, ABq, J = 6. 8 Hz) ,8.33 (1H, s), 8.28and8.05 (2H, A′ B′ q, J = 8. 7 Hz), 7.80 (1H, s), 7.73and7.22(4H,A″B″q, J = 8.7 Hz ), 7.63and7.57 (2H, A″' B″' q, J =7.9Hz), 5.30 (2H, s), 4.34 (1H, b r # t, J = 12. 1 Hz), 3.04 (3H, s), 2.97(3H, s), 2.38-2.18 (2H, m), 2.10 -1.96 (2H, m), 1.93-1.80 (2H, m) ,1.72-1.58 (1H, m), 1.52-1.08 ( 3H, m)

[2167] TABLE 210 >90% Example No. Purity (NMR) 1H NMR (δ) ppm

321 MS 663 (M + 1) 300 MHz, DMSO-d6 11.19 (1H, br , 8.31 (1H, s),8.23and8.02 (2 H, ABq, J = 9. 0 Hz), 7.77 (1H, s), 7 .72and7.23 (4H, A′B′ J = 8. 7 Hz ), 7.59and7.48 (2H, A″B″ q, J = 7. 9 Hz), 7.53and7.51(4H,A″′ B″′ q , J = 9. 0 Hz), 5.16 (2H, s), 4.72-2 # .97 (8H, brm), 4.34(1H, br t, J = 12. 1 Hz), 2.79 (3H, s), 2.38 -2.17 (2H, m), 2.07-1.93(2H, m) 1.93-1.78 (2H, m), 1.69-1.58 ( 1H, m), 1.50-1.10 (3H, m)

322 MS 671 (M + 1) 300 MHz, DMSO-d6 9.54 (1H, t, J = 5. 7 Hz), 8.91 (1H,s), 8.81 (1H, d, J = 4. 9 Hz), 8.48 ( 1H, d, J = 7. 9 Hz), 8.32 (1H, s),8. 27 (1H, d, J = 9. 0 Hz), 8.25 (1H, s) , 8.07-7.97 (3H, m), 7.71and7.25 (4H, ABq, J = 8. 9 Hz), 7.56-7.49 (5H, m), 5.16 (2H, s), 4.59 (2H, d #, J = 5. 6 Hz), 4.36 (1H, br t, J = 12. 4 Hz), 2.37-2.20 (2H, m) ,2.09-1.97 (2H, m), 1.91-1.78 ( 2H, m), 1.70-1.57 (1H, m), 1.50-1.17 (3H,m)

323 MS 671 (M + 1) 300 MHz, DMSO-d6 9.52 (1H, t, J = 6. 0 Hz), 8.72 (1H,d, J = 5. 3 Hz), 8.30-8.19 (4H, m), 8.08 (1H, d, J = 7. 9 Hz), 8.02 (1H,d, J = 7. 6 HZ), 7.77-7.64 (4H, m), 7.57-7.49 (5H, m), 7.24 (2H, d, J=8. 7 Hz), 5.16 (2H, s), 4.77 (2H, d, J = 5. 6 Hz), 4.34 (1H, t, J =12.8 # Hz), 2.36-2.19 (2H, m), 2.07-1. 95 (2H, m), 1.91-1.78 (2H, m), 1.69-1.59 (1H, m), 1.45-1.20 (3H, m)

[2168] TABLE 2H °90% Example No. Purity (NMR) 1H NMR (δ) ppm

324 MS 662 (M + 1) 300 MHz, DMSO-d6 8.36 (1H, d, J = 7. 9 Hz), 8.30 (1H,s), 8.28and8.05 (2H, AEq, J = 8. 8 Hz), 8.16 (1H, s), 7.79and7.46 ( 2H,A′ B′ q, J = 8. 3 Hz), 7.74and7. 25 (4H, A″B″ q, J = 8.9 HZ), 7.52and7.50 (4H, A″′ B″′ q, J = 8. 7 Hz), 5 .14 (2H, s), 4.36 (1H, br # t, J =12. 1 Hz), 3.80 (1H, br s), 2.39-2.18 (2H, m), 2.10-1.9 8 (2H, m),1.93-1.57 (8H, m), 1.4 9-1.04 (8H, m)

325 MS 685 (M + 1) 300 MHz, DMSO-d6 8.86 (1H, t, J = 6. 0 Hz), 8.84and8.00 (4H, ABq, J = 6. 6 Hz), 8.33 (1H , s), 8.27and8.04 (2H, A′ B′ q, J=9. 0 Hz), 8.12 (1H, s), 7.92and7. 46 (2H, A″B″ q, J = 7. 9 Hz), 7.74and7.23 (4H, A″′ B″′ q, J = 9. 0 Hz), 7 # .53and7.49 (4H, A″″B″″ q, J = 9.1 Hz), 5.13 (2H, s), 4.36 (1H, br t, J = 12. 8 Hz), 3.70 (2H, td, J = 6.8, 6. 0 Hz), 3.21 (2H, t, J = 6. 8 Hz) , 2.38-2.20 (2H, m), 2.09-1.95 (2H, m), 1.91-1.77 (2H, m), 1.70-1.59 (1H, m), 1.49-1.20 (3H, m)

326 MS 610 (M + 1) 300 MHz, DMSO-d6 12.80 (1H, brs), 8.23 (1H, s), 7. 90(1H, d, J = 8. 7 Hz), 7.83 (1H, d, J = 8. 7 Hz), 7.60-7.50 (5H, m), 7.39 (2H, d, J = 7. 8 Hz), 7.23-7.10 ( 3H, m), 7.05 (1H, d, J = 7. 8 Hz),6. 85 (1H, s), 3.94 (1H, s), 2.97, 2. 88 (6H, s), 2.30-2.10 (2H, m), 1.# 90-1.50 (5H, m), 1.40-1.00 (3H, m)

[2169] TABLE 212 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

327 MS 583 (M + 1) 300 MHz, DMSO-d6 13.20-12.60 (2H, brs), 8.23 (1H ,s), 7.98 (2H, d, J = 6. 6 Hz), 7.95 (1H, d, J = 8. 7 Hz), 7.87 (1H, d, J=8. 7 Hz), 7.70-7.50 (5H, m), 7.27 -7.20 (3H, m), 7.08 (1H, d, J = 7.8Hz), 6.90 (1H, s), 3.93 (1H, s), 2 .51-2.05 (2H, m), 1.90-1.70 (4H , #m), 1.65-1.55 (1H, m), 1.40-1. 10 (3H, m)

[2170] TABLE 213

Ex. No. R R′ 2001 —H 4-(-Me) 2002 —H 3-(—CF₃) 2003 5-(—F) —H 2004 3-(—F)2-(—F) 2005 3-(—F) 3-(—F) 2006 3-(—F) 4-(—F) 2007 4-(—F) 4-(—F) 20085-(—F) 4-(—F) 2009 6-(—F) 4-(—F) 2010 4-(—F) 4-(—Cl) 2011 5-(—F) 4-(-Me)2012 5-(—F) 4-(—CF₃) 2013 5-(—F) 4-(—CO₂H) 2014 5-(—F) 4-(—CO₂Me) 20155-(—F)

2016 5-(—F) 4-(—CONH₂) 2017 5-(—F) 4-{—CON(Me)₂} 2018 5-(—F) 4-(—OMe)2019 5-(—F) 4-(—SMe) 2020 5-(—F)

2021 5-(—F)

2022 4-(—Cl) —H 2023 4-(—Cl) 4-(—F) 2024 4-(—Cl) 4-(—Cl) 2025 4-(—Cl)4-(-Me) 2026 5-(—Cl) 4-(—CF₃) 2027 4-(—Cl) 4-(—CO₂H) 2028 5-(—Cl)4-(—CO₂MeI 2029 5-(—Cl)

2030 4-(—Cl) 4-(—CONH₂) 2031 5-(—Cl) 4-(—CON(Me)₂} 2032 5-(—Cl) 3-(—OMe)2033 4-(—Cl) 4-(—SMe) 2034 5-(—Cl)

2035 4-(—Cl)

2036 5-(-CN) 4-(—F) 2037 4-(-CN) 4-(—Cl) 2038 5-(—NO₂) 4-(—F) 20394-(—NO₂) 4-(—Cl) 2040 5-(-Me) 4-(—CO₂H) 2041 5-(-Me) 4-(—CO₂Me) 20425-(-Me)

2043 5-(—CF₃) 4-(—CO₂H) 2044 5-(—CF₃) 4-(—CO₂Me) 2045 5-(—CF₃)

2046 5-(—CO₂H) 4-(—F) 2047 4-(—CO₂H) 4-(—Cl) 2048 5-(—CO₂Me) 4-(—F) 20495-(—CO₂Me) 4-(—Cl) 2050 5-(—Ac) 4-(—F) 2051 5-(—Ac) 4-(—Cl) 2052

—H 2053

4-(—F) 2054

4-(—Cl) 2055

4-(-CN) 2056

4-(—No₂) 2057

4-(-Me) 2058

4-(—CF₃) 2059

4-(—Ac) 2060

4-(—CO₂H) 2061

4-(—CO₂Me) 2062

2063

4-(—CONH₂) 2064

4-{—CON (Me)₂} 2065

4-{—C(═NH)NH₂} 2066

4-(—OMe) 2067

2068

4-(—NHMe) 2069

4-(—NHAc) 2070

2071

4-(—SMe) 2072

2073

2074

2075

2076 5-(—CONH₂) —H 2077 5-(—CONH₂) 4-(—F) 2078 5-(—CONH₂)2,3,4,5,6-penta-(—F) 2079 5-(—CONH₂) 2-(—Cl) 2080 5-(—CONH₂) 3-(—Cl)2081 3-(—CONH₂) 2-(—Cl) 2082 3-(—CONH₂) 3-(—Cl) 2083 3-(—CONH₂) 4-(—Cl)2084 4-(—CONH₂) 2-(—Cl) 2085 4-(—CONH₂) 3-(—Cl) 2086 4-(—CONH₂) 4-(—Cl)2087 6-(—CONH₂) 2-(—Cl) 2088 6-(—CONH₂) 3-(—Cl) 2089 6-(—CONH₂) 4-(—Cl)2090 5-(—CONH₂) 3,5-di-(—Cl) 2091 5-(—CONH₂) 4-(-CN) 2092 5-(—CONH₂)4-(—NO₂) 2093 5-(—CONH₂) 4-(-Me) 2094 5-(—CONH₂) 2,6-di-(-Me) 20955-(—CONH₂) 4-(—CF₃) 2096 5-(—CONH₂) 4-(—Ac) 2097 5-(—CONH₂) 4-(—CO₂H)2098 5-(—CONH₂) 4-(—CO₂Me) 2099 5-(—CONH₂)

2100 5-(—CONH₂) 4-(—CONH₂) 2101 5-(—CONH₂) 3,5-di-(—CONH₂) 21025-(—CONH₂) 4-{—CON(Me)₂} 2103 5-(—CONH₂) 4-{—C(═NH)NH₂} 2104 5-(—CONH₂)4-(—OMe) 2105 5-(—CONH₂) 3,4,5-tri-(—OMe) 2106 5-(—CONH₂)

2107 5-(—CONH₂) 4-(—NHMe) 2108 5-(—CONH₂) 4-(—NHAc) 2109 5-(—CONH₂)

2110 5-(—CONH₂) 4-(—SMe) 2111 5-(—CONH₂)

2112 5-(—CONH₂)

2113 5-(—CONH₂)

2114 5-(—CONH₂)

2115 5-{—CON(Me)₂} —H 2116 5-{—CON(Me)₂} 4-(—F) 2117 4-{—CON(Me)₂}4-(—Cl) 2118 5-{—CON(Me)₂} 4-(-CN) 2119 5-{—CON(Me)₂} 4-(—NO₂) 21205-{—CON(Me)₂} 4-(-Me) 2121 4-{—CON(Me)₂} 4-(—CF₃) 2122 5-{—CON(Me)₂}4-(—Ac) 2123 5-{—CON(Me)₂} 4-(—CO₂H) 2124 5-{—CON(Me)₂} 4-(—CO₂Me) 21255-{—CON(Me)₂}

2126 5-{—CON(Me)₂} 3-(—CONH₂) 2127 4-{—CON(Me)₂} 4-{—CON(Me)₂} 21285-{—CON(Me)₂} 4-{—C(═NH)NH₂} 2129 5-{—CON(Me)₂} 4-(—OMe) 21305-{—CON(Me)₂}

2131 5-{—CON(Me)₂} 4-(—NHMe) 2132 5-{—CON(Me)₂} 4-(—NHAc) 21335-{—CON(Me)₂}

2134 4-{—CON(Me)₂} 4-(—SMe) 2135 5-{—CON(Me)₂}

2136 4-{—CON(Me)₂}

2137 5-{—CON(Me)₂}

2138 5-{—CON(Me)₂}

2139 5-(—OMe) —H 2140 5-(—OMe) 4-(—F) 2141 3-(—OMe) 4-(—Cl) 21424-(—OMe) 4-(—Cl) 2143 5-(—OMe) 2-(—Cl) 2144 5-(—OMe) 3-(—Cl) 21456-(—OMe) 4-(—Cl) 2146 5-(—OMe) 4-(-CN) 2147 5-(—OMe) 4-(—NO₂) 21485-(—OMe) 4-(-Me) 2149 5-(—OMe) 4-(—CF₃) 2150 5-(—OMe) 4-(—Ac) 21514-(—OMe) 4-(—CO₂H) 2152 4,5-di-(—OMe) 4-(—CO₂H) 2153 5-(—OMe) 4-(—CO₂Me)2154 5-(—OMe)

2155 5-(—OMe) 4-(—CONH₂) 2156 5-(—OMe) 4-{—CON(Me)₂} 2157 5-(—OMe)4-{—C(═NH)NH₂} 2158 5-(—OMe) 4-(—OMe) 2159 5-(—OMe)

2160 5-(—OMe) 4-(—NHMe) 2161 5-(—OMe) 4-(—NHAc) 2162 5-(—OMe)

2163 5-(—OMe) 4-(—SMe) 2164 5-(—OMe)

2165 5-(—OMe)

2166 5-(—OMe)

2167 5-(—OMe)

2168 5-(—NHMe) 4-(—F) 2169 5-(—NHMe) 4-(—Cl) 2170 5-(—NHAc) 4-(—F) 21715-(—NHAc) 4-(—Cl) 2172 5-(—NHAc) 4-(—Ac) 2173 5-(—NHAc) 4-(—CONH₂) 21745-(—NNAc) 4-{—CON(Me)₂} 2175

4-(—F) 2176

4-(—Cl) 2177

4-(-Me) 2178

4-(—CF₃) 2179

4-(—CO₂H) 2180

4-(—CO₂Me) 2181

2182

4-(—SMe) 2183

2184

2185 5-(—SMe) 4-(—F) 2186 4-(—SMe) 4-(—Cl) 2187 5-(—SMe) 4-(-Me) 21885-(—SMe) 4-(—CF₃) 2189 5-(—SMe) 4-(—Ac) 2190 5-(—SMe) 4-(—CONH₂) 21915-(—SMe) 4-{—CON(Me)₂} 2192

4-(—F) 2193

4-(—Cl) 2194

4-(-Me) 2195

4-(—CF₃) 2196

4-(—Ac) 2197

4-(—CONH₂) 2198

4-{—CON(Me)₂} 2199

4-(—F) 2200

4-(—Cl) 2201

4-(-Me) 2202

4-(—CF₃) 2203

4-(—Ac) 2204

4-(—CONH₂) 2205

4-{—CON(Me)₂} 2206

4-(—F) 2207

4-(—Cl) 2208

2,4-di-(—Cl) 2209

4-(-Me) 2210

3-(—CF₃) 2211

4-(—CF₃) 2212

4-(—CONH₂) 2213

4-{—CON(Me)₂} 2214

4-(—SMe) 2215

2216

2217

4-(—F) 2218

4-(—Cl) 2219

4-(-Me) 2220

4-(—CF₃) 2221

4-(—CONH₂) 2222

4-{—CON(Me)₂} 2223

4-(—SMe) 2224

2225

2226 5-{—O—(CH₂)₂—OH} 4-(—Cl) 2227 5-{—O—(CH₂)₃—OH} 4-(—Cl) 2228

4-(—Cl) 2229

4-(—Cl) 2230

4-(—Cl) 2231

4-(—Cl) 2232

4-(—Cl) 2233

4-(—Cl) 2234

4-(—Cl) 2235

4-(—Cl) 2236

4-(—Cl) 2237

4-(—Cl) 2238

4-(—Cl) 2239

4-(—Cl) 2240

4-(—Cl) 2241

4-(—Cl) 2242

4-(—Cl) 2243

4-(—Cl) 2244

4-(—Cl) 2245

4-(—Cl) 2246

4-(—Cl) 2247

4-(—Cl) 2248

4-(—Cl) 2249

4-(—Cl) 2250

4-(—Cl) 2251

4-(—Cl) 2252

4-(—Cl) 2253

4-(—Cl) 2254

4-(—Cl)

[2171] TABLE 214

Ex. No. R R′ 2255 —H —H 2256 —H 4-(-Me) 2257 —H 3-(—CF₃) 2258 5-(—F) —H2259 5-(—F) 4-(—F) 2260 5-(—F) 4-(—Cl) 2261 5-(—F) 4-(-Me) 2262 5-(—F)4-(—CF₃) 2263 5-(—F) 4-(—CO₂H) 2264 5-(—F) 4-(—CO₂Me) 2265 5-(—F)

2266 5-(—F) 4-(—CONH₂) 2267 5-(—F) 4-{—CON(Me)₂} 2268 5-(—F) 4-(—OMe)2269 5-(—F) 4-(—SMe) 2270 5-(—F)

2271 5-(—F)

2272 4-(—Cl) —H 2273 5-(—Cl) 4-(—F) 2274 4-(—Cl) 4-(—Cl) 2275 5-(—Cl)4-(-Me) 2276 5-(—Cl) 4-(—CF₃) 2277 5-(—Cl) 4-(—CO₂H) 2278 5-(—Cl)4-(—CO₂Me) 2279 5-(—Cl)

2280 5-(—Cl) 4-(—CONH₂) 2281 5-(—Cl) 4-{—CON(Me)₂} 2282 5-(—Cl) 4-(—OMe)2283 5-(—Cl) 4-(—SMe) 2284 5-(—Cl)

2285 5-(—Cl)

2286 5-(-CN) 4-(—F) 2287 5-(-CN) 4-(—Cl) 2288 5-(—NO₂) 4-(—F) 22895-(—NO₂) 4-(—Cl) 2290 5-(-Me) 4-(—CO₂H) 2291 5-(-Me) 4-(—CO₂Me) 22925-(-Me)

2293 5-(—CF₃) 4-(—CO₂H) 2294 5-(—CF₃) 4-(—CO₂Me) 2295 5-(—CF₃)

2296 5-(—CO₂H) 4-(—F) 2297 4-(—CO₂H) 4-(—Cl) 2298 5-(—CO₂Me) 4-(—F) 22995-(—CO₂Me) 4-(—Cl) 2300 5-(—Ac) 4-(—F) 2301 5-(—Ac) 4-(—Cl) 2302

—H 2303

4-(—F) 2304

4-(—Cl) 2305

4-(-CN) 2306

4-(—NO₂) 2307

4-(-Me) 2308

4-(—CF₃) 2309

4-(—Ac) 2310

4-(—CO₂H) 2311

4-(—CO₂Me) 2312

2313

4-(—CONH₂) 2314

4-{—CON(Me)₂} 2315

4-{—C(═NH)NH₂} 2316

4-(—OMe) 2317

2318

4-(—NHMe) 2319

4-(—NHAc) 2320

2321

4-(—SMe) 2322

2323

2324

2325

2326 5-(—CONH₂) —H 2327 5-(—CONH₂) 4-(—F) 2328 4-(—CONH₂) 4-(—Cl) 23295-(—CONH₂) 4-(-CN) 2330 5-(—CONH₂) 4-(—NO₂) 2331 5-(—CONH₂) 4-(-Me) 23325-(—CONH₂) 4-(—CF₃) 2333 5-(—CONH₂) 4-(—Ac) 2334 5-(—CONH₂) 4-(—CO₂H)2335 5-(—CONH₂) 4-(—CO₂Me) 2336 5-(—CONH₂)

2337 5-(—CONH₂) 4-(—CONH₂) 2338 5-(—CONH₂) 4-{—CON(Me)₂} 2339 5-(—CONH₂)4-{—C(═NH)NH₂} 2340 5-(—CONH₂) 4-(—OMe) 2341 5-(—CONH₂)

2342 5-(—CONH₂) 4-(-13 NHMe) 2343 5-(—CONH₂) 4-(—NHAc) 2344 5-(—CONH₂)

2345 5-(—CONH₂) 4-(—SMe) 2346 5-(—CONH₂)

2347 5-(—CONH₂)

2348 5-(—CONH₂)

2349 5-(—CONH₂)

2350 5-{—CON(Me)₂} —H 2351 5-{—CON(Me)₂} 4-(—F) 2352 4-{—CON(Me)₂}4-(—Cl) 2353 5-{—CON(Me)₂} 4-(-CN) 2354 5-{—CON(Me)₂} 4-(—NO₂) 23555-{—CON(Me)₂} 4-(-Me) 2356 5-{—CON(Me)₂} 4-(—CF₃) 2357 5-{—CON(Me)₂}4-(—Ac) 2358 5-{—CON(Me)₂} 4-(—CO₂H) 2359 5-{—CON(Me)₂} 4-(—CO₂Me) 23605-{—CON(Me)₂}

2361 5-{—CON(Me)₂} 4-(—CONH₂) 2362 5-{—CON(Me)₂} 4-(—CON(Me)₂} 23635-{—CON(Me)₂} 4-{—C(═NH)NH₂} 2364 5-{—CON(Me)₂} 4-(—OMe) 23655-(—CON(Me)₂}

2366 5-{—CON(Me)₂} 4-(—NHMe) 2367 5-{—CON(Me)₂} 4-(—NHAc) 23685-{—CON(Me)₂}

2369 5-{—CON(Me)₂} 4-(—SMe) 2370 5-(—CON(Me)₂}

2371 5-(—CON(Me)₂}

2372 5-{—CON(Me)₂}

2373 5-(—CON(Me)₂}

2374 5-(—OMe) —H 2375 5-(—OMe) 4-(—F) 2376 5-(—OMe) 4-(—Cl) 23775-(—OMe) 4-(-CN) 2378 5-(—OMe) 4-(—NO₂) 2379 5-(—OMe) 4-(-Me) 23805-(—OMe) 4-(—CF₃) 2381 5-(—OMe) 4-(—Ac) 2382 5-(—OMe) 4-(—CO₂H) 23835-(—OMe) 4-(—CO₂Me) 2384 5-(—OMe)

2385 5-(—OMe) 4-(—CONH₂) 2386 5-(—OMe) 4-{—CON(Me)₂} 2387 5-(—OMe)4-{—C(═NH)NH₂} 2388 5-(—OMe) 4-(—OMe) 2389 5-(—OMe)

2390 5-(—OMe) 4-(—NHMe) 2391 5-(—OMe) 4-(—NHAc) 2392 5-(—OMe)

2393 5-(—OMe) 4-(—SMe) 2394 5-(—OMe)

2395 5-(—OMe)

2396 5-(—OMe)

2397 5-(—OMe)

2398 5-(—NHMe) 4-(—F) 2399 5-(—NHMe) 4-(—Cl) 2400 5-(—NHAc) 4-(—F) 24015-(—NHAc) 4-(—Cl) 2402 5-(—NHAc) 4-(—Ac) 2403 5-(—NHAc) 4-(—CONH₂) 24045-(—NHAc) 4-{—CON(Me)₂} 2405

4-(—F) 2406

4-(—Cl) 2407

4-(-Me) 2408

4-(—CF₃) 2409

4-(—CO₂H) 2410

4-(—CO₂Me) 2411

2412

4-(—SMe) 2413

2414

2415 5-(—SMe) 4-(—F) 2416 5-(—SMe) 4-(—Cl) 2417 5-(—SMe) 4-(-Me) 24185-(—SMe) 4-(—CF₃) 2419 5-(—SMe) 4-(—Ac) 2420 5-(—SMe) 4-(—CONH₂) 24215-(—SMe) 4-{—CON(Me)₂} 2422

4-(—F) 2423

4-(—Cl) 2424

4-(-Me) 2425

4-(—CF₃) 2426

4-(—Ac) 2427

4-(—CONH₂) 2428

4-{-CON(Me)₂} 2429

4-(—F) 2430

4-(—Cl) 2431

4-(-Me) 2432

4-(—CF₃) 2433

4-(—Ac) 2434

4-(—CONH₂) 2435

4-{—CON(Me)₂} 2436

4-(—F) 2437

4-(—Cl) 2438

4-(-Me) 2439

4-(—CF₃) 2440

4-(—CONH₂) 2441

4-{—CON(Me)₂} 2442

4-(—SMe) 2443

2444

2445

4-(—F) 2446

4-(—Cl) 2447

4-(-Me) 2448

4-(—CF₃) 2449

4-(—CONH₂) 2450

4-{—CON(Me)₂} 2451

4-(—SMe) 2452

2453

[2172] TABLE 215

Ex. No. R R′ 2454 2-(—F) 2-(—F) 2455 2-(—F) 3-(—F) 2456 2-(—F) 4-(—F)2457 3-(—Cl) 3-(—Cl) 2458 3,5-di-(—Cl) 3,5-di-(—Cl) 2459 3-(-CN) 3-(-CN)2460 3-(—NO₂) 3-(—NO₂) 2461 3-(-Me) 3-(-Me) 2462 3-(—CF₃) 3-(—CF₃) 24633-(—Ac) 3-(—Ac) 2464 3—(—CO₂H) 3-(—CO₂H) 2465 3-(—CO₂Me) 3-(-CO₂Me) 2466

2467 3-(—CONH₂) 3-(—CONH₂₎ 2468 3-(—CONH₂) 3-(—F) 2469 3-(—CONH₂)3-(—Cl) 2470 3-{—CON(Me)₂} 3-{—CON(Me)₂} 2471 3-{—CON(Me)₂} 3-(—F) 24723-{—CON(Me)₂} 3-(—Cl) 2473 3-{—C(═NH)NH₂} 3-{—C(═NH)NH₂} 2474 3-(—OMe)3-(—OMe) 2475

2476 3-(—NHMe) 3-(—NHMe) 2477 3-(—NHAc) 3-(—NHAc) 2478

2479 3-(—SMe) 3-(—SMe) 2480

2481

2482

2483

2484 3-(—F) 4-(—F) 2485 3-(—Cl) 4-(—Cl) 2486 4-(-CN) 4-(-CN) 24874-(—NO₂) 4-(—NO₂) 2488 3-(-Me) 4-(-Me) 2489 4-(-Me) 2,6-di-(-Me) 24904-(—CF₃) 4-(—CF₃) 2491 4-(—Ac) 4-(—Ac) 2492 4-(—CO₂H) 4-(—CO₂H) 24934-(—CO₂Me) 4-(—CO₂Me) 2494

2495 4-(—CONH₂) 4-(—CONH₂) 2496 4-(—CONH₂) 4-(—F) 2497 4-(—CONH₂)2,3,4,5,6-penta-(—F) 2498 4-(—CONH₂) 4-(—Cl) 2499 4-{—CON(Me)₂}4-{—CON(Me)₂} 2500 4-{—CON(Me)₂} 4-(—F) 2501 4-{—CON(Me)₂} 4-(—Cl) 25024-{—CON(Me)₂} 3,5-di-(—Cl) 2503 4-{—C(═NH)NH₂} 4-{—C(═NH)NH₂} 25044-(—OMe) 4-(—OMe) 2505 4-(—OMe) 3,4,5-tri-(—OMe) 2506

2507 4-(—NHMe) 4-(—NHMe) 2508 4-(—NHAc) 4-(—NHAc) 2509

2510 4-(—SMe) 4-(—SMe) 2511

2512

2513

2514

[2173] TABLE 216

Ex. No. R R′ 2515 —H —H 2516 2-(—F) 3-(—F) 2517 3-(—Cl) 3-(—Cl) 25183-(-CN) 3-(-CN) 2519 3-(—NO₂) 3-(—NO₂) 2520 3-(-Me) 3-(-Me) 25213-(—CF₃) 3-(—CF₃) 2522 3-(—Ac) 3-(—Ac) 2523 3-(—CO₂H) 3-(—CO₂H) 25243-(—CO₂Me) 3-(—CO₂Me) 2525

2526 3-(—CONH₂) 3-(—CONH₂) 2527 3-(—CONH₂) 3-(—F) 2528 3-(—CONH₂)3-(—Cl) 2529 3-{—CON(Me)2} 3-{—CON(Me)2} 2530 3-{—CON(Me)2} 3-(—F) 25313-{—CON(Me)2} 3-(—Cl) 2532 3-{—C(═NH)NH₂} 3-{—C(═NH)NH₂} 2533 3-(—OMe)3-(—OMe) 2534

2535 3-(—NHMe) 3-(—NHMe) 2536 3-(—NHAc) 3-(—NHAc) 2537

2538 3-(—SMe) 3-(—SMe) 2539

2540

2541

2542

2543 3-(—F) 4-(—F) 2544 4-(—Cl) 4-(—Cl) 2545 4-(-CN) 4-(-CN) 25464-(—NO₂) 4-(—NO₂) 2547 4-(-Me) 4-(-Me) 2548 4-(—CF₃) 4-(—CF₃) 25494-(—Ac) 4-(—Ac) 2550 3-(—CO₂H) 4-(—CO₂H) 2551 4-(—CO₂Me) 4-(—CO₂Me) 2552

2553 4-(—CONH₂) 4-(—CONH₂) 2554 4-(—CONH₂) 4-(—F) 2555 4-(—CONH₂)4-(—Cl) 2556 3-{—CON(Me)₂} 4-{—CON(Me)₂} 2557 3-{—CON(Me)₂} 4-(—F) 25584-{—CON(Me)₂} 4-(—Cl) 2559 4-{—C(═NH)NH₂} 4-{—C(═NH)NH₂} 2560 4-(—OMe)4-(—OMe) 2561

2562 4-(—NHMe) 4-(—NHMe) 2563 4-(—NHAc) 4-(—NHAc) 2564

2565 4-(—SMe) 4-(—SMe) 2566

2567

2568

2569

[2174] TABLE 217

Py: pyridyl group Ex. No. Py R′ 2570 3-Py —H 2571 3-Py 3-(—F) 2572 3-Py3-(—Cl) 2573 3-Py 3-(-Me) 2574 3-Py 3-(—CF₃) 2575 3-Py 3-(—Ac) 2576 3-Py3-(—CO₂H) 2577 3-Py 3-(—CO₂Me) 2578 3-Py

2579 3-Py 3-(—CONH₂) 2580 3-Py 3-{—CON(Me)₂} 2581 3-Py 4-(—F) 2582 3-Py4-(—Cl) 2583 3-Py 4-(-Me) 2584 3-Py 4-(—CF₃) 2585 3-Py 4-(—Ac) 2586 2-Py4-(—CO₂H) 2587 3-Py 4-(—CO₂Me) 2588 3-Py

2589 4-Py 4-(—CONH₂) 2590 3-Py 4-{—CON(Me)₂}

[2175] TABLE 218

Py: pyridyl group Ex. No. Py R′ 2591 3-Py H 2592 3-Py 3-(—F) 2593 3-Py3-(—Cl) 2594 3-Py 3-(-Me) 2595 3-Py 3-(-CF₃) 2596 3-Py 3-(—Ac) 2597 3-Py3-(—CO₂H) 2598 3-Py 3-(—CO₂Me) 2599 3-Py

2600 3-Py 3-(—CONH₂) 2601 3-Py 3-{—CON(Me)₂} 2602 3-Py 4-(—F) 2603 3-Py4-(—Cl) 2604 3-Py 4-(-Me) 2605 3-Py 4-(—CF₃) 2606 3-Py 4-(—Ac) 2607 3-Py4-(—CO₂H) 2608 3-Py 4-(—CO₂Me) 2609 3-Py

2610 3-Py 4-(—CONH₂) 2611 3-Py 4-{—CON(Me)₂}

[2176] TABLE 219 >90% Example No. Purity (NMR) 1H NMR (δ) ppm

328 MS 662 (M + 1) 300 MHz, DMSO-d6 8.29(1H, s), 8.23 (1H, d, J = 9.0Hz), 8.02(1H, d, J = 8. 4 Hz), 7.8 0(1H, s), 7.71(2H, d, J = 8. 4 Hz) ,7.61 (1H, d, J = 9. 3 Hz), 7.55-7 .45 (3H, m), 7.46 (2H, d, J = 8. 1Hz), 7.22(2H, d, J = 8. 7 Hz), # 5.16 (2H, s,), 4.34 (1H, m), 4.20-3.40(4H, m), 2.60-2.15 (6H, m), 2 .1O-1.90(2H,m), 1.85-1.70(2 H, m),1.65-1.55(1H, m), 1.50-1.10(3H, m)

329 MS 553 (M + 1) 400 MHz, DMSO-d6 9.80 (1H, brs), 8.32 (1H, s), 8.30(1H, d, J = 8. 8 Hz), 8.06 (1H, d, J =8. 8 Hz), 7.74 (2H, d, J = 8. 6Hz), 7.48-7.37 (4H, m), 7.22 (1H, d, J =8. 6 Hz), 7.17 (1H, d, J = 8. 2Hz), 7.05 (1H, d, J = 2. 3 Hz), 6.88 (1H, ##dd, J = 8. 3, 2. 5 Hz), 5.04(2H, s), 4.37 (1H, m), 2.37-2.22 (2H, m), 2.11-1.98 (2H, m), 1.93-1.81(2 H, m), 1.70-1.58 (1H, m), 1.56-1 .22 (3H, m)

330 MS 622 (M + 1) 300 MHz, DMSO-d6 8.38 (1H, d, J = 7. 5 Hz), 8.32 (1H,s), 8.29 (1H, d, J = 9. 9 Hz), 8.16 ( 1H, s), 8.05 (1H, d, J = 9. 0 Hz),7. 96 (1H, d, J = 7. 5 Hz), 7.75 (2H, d, J = 8. 4 Hz), 7.53-7.43 (5H,m), 7. 25 (2H, d, J = 8. 4 Hz), 5.13 (2H, s) , 4.36 (1H, m), 4.12 (1H,sept, J = # 6.9 Hz), 2.40-2.15 (2H, m), 2.10 -1.95 (2H, m), 1.90-1.75(2H, m) 1.70-1.55 (1H, m), 1.50-1.20 ( 3H, m), 1.18 (6H, d, J = 6. 6 Hz)

[2177] TABLE 220 >90% Example No. Purity (NMR) 1H NMR (δ) ppm

331 MS 636 (M + 1) 300 MHz, DMSO-d6 8.31 (1H, s), 8.27 (1H, d, J = 8. 7Hz), 8.05 (1H, d, J = 8. 7 Hz), 7.75-7.41 (9H, m), 7.23 (2H, d, J = 8. 7Hz), 4.36 (1H, m), 4.00-3.90 (1H, m), 2.84 (3H, brs), 2.40-2.15 (2 H, m),2.10-2.00 (2H, m), 1.95-1 .75(2H, m), 1.70-1.55 (1H, m), 1 .50-1.00 (7H,m)

332 MS 656 (M + 1) 300 MHz, DMSO-d6 10.42 (1H, s), 8.29 (1H, s), 8.27(1H, s), 8.10 (1H, d, J = 7. 9 Hz), 8 .03 (1H, d, J = 8. 6Hz), 7.82 (2H,d , J = 7. 5 Hz), 7.73 (2H, d, J = 8. 7 Hz ), 7.56-7.52 (5H, m), 7.38(2H, t , J = 7. 9 Hz), 7.26 # (2H, d, J = 8. 7 Hz ), 7.13 (1H, t, J = 7.5 Hz), 5.20 (2 H, s), 4.35 (1H, br t, J = 11. 7 Hz), 2.37-2.19 (2H, m) ,2.07-1.96 (2H, m), 1.92-1.79 ( 2H, m), 1.69-1.58 (1H, m), 1.50-1.20 (3H,m)

333 MS 678 (M + 1) 300 MHz, DMSO-d6 8.30 (1H, s), 8.24 and 8.03 (2H, ABq, J = 8. 8 Hz), 7.71 and 7.22 (4H, A′ B′ q, J = 8. 8 Hz), 7.69 (1H,s), 7 .52 (4H, s), 7.50 and 7.43 (2H, A″B″ q, J = 7. 7 Hz), 5.15 (2H, s)4.35 (1H, br t, J = 12. 1 Hz), 4.05-3.15 (5H, br # m), 3.27 (3H, s),2.39-2.20 (2H, m), 2.07-1.75 (6H, m), 1.70-1.5 8 (1H, m) 1.55-1.20 (5H,m)

[2178] TABLE 221 >90% Example No. Purity (NMR) 1H NMR (δ) ppm

334 MS 611 (M + 1) 300 MHz, DMSO-d6 8.22 (1H, d, J = 1. 5 Hz), 8.01 (1H,d, J = 9. 0 Hz), 7.89 (1H, dd, J = 8. 6 , 1.5 Hz), 7.61 (2H, d, J = 8. 6Hz), 7.50-7.39 (4H, m), 7.27 (1H, d, J =8. 6 Hz), 7.22 (1H, d, J = 2. 6Hz), 7.13 (2H, d, J = 8. 6 Hz), 7.04 (1H, # dd, J = 8. 2, 2. 6 Hz), 5.04(2H, s), 4.28 (1H, m), 4.11 (2H, t, J = 6. 3H z), 3.57 (2H, t, J = 6. 3Hz), 2.38-2.17 (2H, m), 2.00-1.79 (6H, m), 1.70-1.59 (1H, m), 1.52-1.16(3 H, m)

335 MS 597 (M + 1) 300 MHz, DMSO-d6 8.30 (1H, d, J = 1. 5 Hz), 8.27 (1H,d, J = 9. 0 Hz), 8.04 (1H, dd, J = 8. 6 , 1.5 Hz), 7.72 (2H, d, J = 9. 9Hz), 7.60-7.40 (4H, m), 7.32-7.19 (4 H, m), 7.06 (1H, dd, J = 8. 6, 3. 0Hz ), 5.08 (2H, s), 4.36 (1H, m), 4.0 6 (2H, t, J = 4. 8 Hz), 3.74 (2H,t, J = # 4.8 Hz), 2.38-1.19 (2H, m) 2.1 3-1.97 (2H, m), 1.94-1.78 (2H, m), 1.72-1.59 (1H, m), 1.52-1. 20 (3H, m)

[2179] TABLE 222 HCV polymerase HCV polymerase Ex. inhibitory activityEx. inhibitory activity No. IC₅₀ [μM] No. IC₅₀ [μM] 340 0.017 360 0.014341 0.025 361 0.028 342 0.015 362 0.020 343 0.017 363 0.11 344 0.016 3640.12 345 0.012 365 0.020 346 0.025 366 0.024 347 0.022 367 0.011 3480.013 368 0.024 349 0.021 369 0.022 350 0.020 370 0.017 351 0.019 3710.015 352 0.013 372 0.033 353 0.023 373 0.013 354 0.013 372 0.013 3550.015 375 0.012 356 0.016 376 0.014 357 0.019 377 0.012 358 0.017 3780.018 359 0.015 379 0.021

[2180] TABLE 223 HCV polymerase HCV polymerase Ex. inhibitory activityEx. inhibitory activity No. IC₅₀ [μM] No. IC₅₀ [μM] 380 0.023 409 0.020381 0.011 410 0.018 382 0.015 411 0.015 383 0.013 412 0.019 384 0.016413 0.026 385 0.019 414 0.024 386 0.018 415 0.019 387 0.025 416 0.024388 0.020 417 0.029 389 0.012 418 0.016 390 0.014 419 0.021 391 0.017420 0.015 392 0.014 421 0.017 393 0.011 422 0.017 394 0.019 423 0.017395 0.016 424 0.020 396 0.025 425 0.026 397 0.037 426 0.053 398 0.077427 0.020 399 0.032 428 0.026

[2181] TABLE 224 HCV polymerase HCV polymerase Ex. inhibitory activityEx. inhibitory activity No. IC₅₀ [μM] No. IC₅₀ [μM] 429 0.017 442 0.024430 0.017 443 0.030 431 0.015 445 0.33 432 0.022 446 0.016 433 0.014 5020.024 434 0.011 503 0.196 435 0.012 601 0.32 436 0.026 701 0.052 4400.070

[2182] TABLE 225 >90% Example No. Purity (NMR) 1H NMR (δ) ppm

341 MS 662 (M + 1) 300 MHz, DMSO-d6 8.29 (1H, d, J = 1. 5 Hz), 8.25 (1H, d, J = 8. 7 Hz), 8.03 (1H, dd, J = 8 .7 Hz), 7.72 and 7.22 (4H, Abq, J=8. 8 Hz), 7.67 (1H, d, J = 1. 5 Hz) , 7.52 (4H, s), 7.49 (1H, dd, J = 7.9, 1. 5 Hz), 7.43 (1H, d, J = 7.9 H z), 4.46 (1H, brs), 4.35 (1H hr #t, J = 12. 4 Hz), 3.62 (1H, brs ), 3 .06 (1H, brs), 2.79 (1H, brs), 2.38-2.20 (2H, brm), 2.08-1.81 (4H, brm), 1.77-1.52 (4H, brm) , 1.46-1.20(3H, brm), 1.19-1. 00 (2H, brm), 0.94 and 0.92 (tot al3H, each s)

342 MS 679 (M + 1) 300 Mz, DMSO-d6 8.28 (1H, d, J = 1. 5 Hz), 8.26 (1H,d, J = 1.8 Hz), 8.19 (1H, d, J = 8. 8 H z), 8.07 (1H, dd, J = 7. 7, 1. 8Hz), 8.00 (1H, dd, J = 8. 8, 1. 5 Hz), 7.7 0 and 7.22 (4H, Abq, J = 8. 8Hz) 7. 56-7.50 (1H, m), 7.56 (4H, s), 5. 17 (2H, s), 4.33 (1H, brt, J =12. 5 # Hz), 2.05 (3H, s), 2.37-2.20 (2H , brm), 2.06-1.80 (4H, brm),1.7 0-1.60 (1H, brm), 1.50-1.20 (3H , brm)

343 MS 694 (M + 1) 300 MHz, DMSO-d6 8.20 (1H, d, J = 1. 5 Hz), 7.93 (1H,d, J = 8. 6 Hz), 7.84 (1H, dd, J = 8. 3 Hz, 1. 5 Hz), 7.57 (2H, d, J =8. 6 Hz ), 7.50-7.40 (4H, m), 7.27 (1H, d , J = 8. 2 Hz), 7.22 (1H, d, J= 2. 6 Hz ), 7.10 (2H, d, J = 8. 6 Hz) 7.01 (1H # , dd, J = 8. 6 Hz, 2.6Hz), 5.02 (2H, s), 4.89 (2H, s), 4.78 (1H, d, J = 4 .1 Hz), 4.38-4.18(1H, m), 3.96-3.81 (1H, m), 3.78-3.62 (2H, m), 3.27-2.99 (2H, m),2.35-1.15 (1 4H, m)

[2183] TABLE 226 >90% Example No. Purity (NMR) 1H NMR (δ) ppm

344 MS 611 (M + 1) 300 MHz, DMSO-d6 8.30 (1H, s), 8.23 (1H, d, J = 8. 7H z), 8.02 (1H, d, J = 8. 4 Hz). 7.71 ( 2H, d, J = 8. 7 Hz), 7.55-7.15(8H, m), 7.07 (1H, dd, J = 8. 4 Hz, 3. 0 Hz ), 5.07 (2H, s), 4.35 (1H,m), 4.1 7 (2H, t, J = 4. 5 Hz), 3.69 (2H, t, J =4. 5 Hz), 3.32 (3H, s),2.40-2.1 # 5 (2H, m), 2.10-1.80 (4H, m), 1.7 5-1.60 (1H, m), 1.50-1.20(3H, m )

345 MS 655 (M + 1) 300 MHz, DMSO-d6 8.29 (1H, d, J = 1. 5 Hz), 8.22 (1H,d, J = 8. 7 Hz), 8.01 (1H, d, J = 8. 7 H z), 7.70 (1H, d, J = 8. 7 Hz),7.50-7.15 (8H, m), 7.07 (1H, dd, J = 8. 4 Hz, 2.4 Hz), 5.07 (2H, s),4.35 (1 H, m), 4.17 (2H, t, J = 4. 2 Hz), 3.7 6 (2H, t, J = 4. 5 Hz),3.65-3.40 (4 # H, m), 3.25 (3H, s), 2.40-2.20 (2 H, m), 2.10-1.80 (4H,m), 1.75-1 .65 (1H, m), 1.65-1.20 (3H, m)

346 MS 621 (M + 1) 300 Mz, DMSO-d6 8.26 (1H, d, J = 1. 9 Hz), 8.23 (1H,d, J = 1. 5 Hz), 8.08-8.02 (2H, m), 7.91 (1H, dd, J = 8. 7, 1.5 Hz), 7.63 and 7.16 (4H, Abq, J = 8. 9 Hz), 7. 56-7.51 (5H, m), 5.15 (2H, s), 4.29 (1H, brt, J = 11. 7 Hz), 2.96 (2H , d, J = 6. 9 Hz), 2.37-2 12 (3H,m) # , 2.00-1.79 (4H, brm), 1.71-1.6 0 (1H, brm) 1.49-1.19 (3H, brm),0.97 and 0.95 (total 6H, each s)

[2184] TABLE 227 >90% Example No. Purity (NMR) 1H NMR (δ) ppm

347 MS 634 (M + 1) 300 Mz, DMSO-d6 8.26 (1H, s), 8.22 (1H, s), 8.06 (1H, 2), 8.05 (1H, d, J = 8. 0 Hz), 7. 94 and 7.85 (2H, ABq, J = 8. 8Hz), 7 .59and7.15 (4H, A′ B′ q, J = 8. 6 Hz ), 7.52 (4H, s), 7.44 (1H,d, J = 8. 0 Hz), 5.12 (2H, s), 4.27 (1H, brt , J = 11. 4 Hz), 2.38-2.18(2H, brm # ), 1.97-1.77 (4H, brm, 1.70-1. 59(1H, brm), 1.49-1.17 (3H,brm )

348 MS 680 (M + 1) 300 MHz, DMSO-d6 8.32 (1H, s), 8.29 (1H, d, J = 9. 0H z), 8.06 (1H, d, J = 8. 7 Hz), 7.74 ( 2H, d, J = 9. 0 Hz), 7.72 (1H,brs), 7.60-7.45 (5H, m), 7.42 (1H, d, J =7. 8 Hz), 7.24 (2H, d, J = 8. 7Hz), 5.15 (2H, s), 4.37 (1H, m), 4.00-3.10 (6H, m), 2.40-2.18 (2H, m), #2.15-1.95 (2H, m), 1.90-1.80 (2 H, m), 1.75-1.20 (6H, m)

349 MS 619 (M + 1) 300 MHz, DMSO-d6 8.41 (1H, d, J = 1. 5 Hz), 8.33 (1H,d, J = 1. 5 Hz), 8.26 (1H, d, J = 8. 7 H z), 8.18 (1H, dd, J = 2. 0 Hz,8. 0 Hz ), 8.04 (1H, dd, J = 1. 5 Hz, 9.0 Hz) , 7.75 (2H, d, J = 8. 7Hz), 7.63 (1H , d, J = 8. 1 Hz), 7.62-7.45 (4H, m) # 7.26 (2H, d, J = 8.7 Hz), 5.25 (2H s), 4.35 (1H, m), 2.45 (3H, s), 2 .40-2.18 (2H, m),2.15-1.95 (2H , m), 1.90-1.80 (2H, m), 1.75-1. 55 (1H, m), 1.50-1.20(3H, m)

[2185] TABLE 228 >90% Example No. Purity (NMR) 1H NMR (δ) ppm

350 MS 622 (M + 1) 300 MHz, DMSO-d6 8.36 (1H, d, J = 7. 7 Hz), 8.29 (1H,s), 8.23 (1H, d, J = 8. 8 Hz), 8.02 ( 1H, d, J = 8. 6 Hz), 7.94 (1H, d,J = 7 .9 Hz), 7.84 (1H, d, J = 1. 6 Hz), 7. 80-7.65 (3H, m), 7.53 (4H,s), 5. 15 (2H, s), 4.34 (1H, m), 4.12 # (1H , m), 2.35-2.20 (2H, m),2.10-1. 60 (5H, m), 1.50-1.20 (3H, m), 1. 17 (6H, d, J = 6. 5 Hz)

351 MS 648 (M + 1) 300 MHz, DMSO-d6 8.29 (1H, s), 8.24 (1H, d, J = 8. 8H z), 8.02 (1H, d, J = 8. 6 Hz), 7.80-7.65 (3H, m), 7.55-7.45 (5H, m),7.32 (1H, d, J = 1. 5 Hz), 7.22 (2H, d, J = 8. 8 Hz), 5.13 (2H, s), 4.35( 1H, m), 3.60 (2H, m), 3.33 (2H, m) # , 2.40-2.15 (2H, m), 2.40-2.15 (14H, m)

352 MS 652 (M + 1) 300 MHZ, DMSO-d6 13.20 (1H, brs), 8.30-8.24 (2H, m),8.13 (1H, s), 8.04 (1H, d, J = 8 .7 Hz), 7.94 (1H, d, J = 8. 0 Hz), 7.75-7.70 (3H, m), 7.55-7.43 (5H, m), 7.25 (2H, d, J = 8. 7 Hz), 5.13 (2H, s), 4.36 (1H, m), 3.53 (2H, s) , # 2.40-2.18 (2H, m), 2.15-1.95 (2H, m), 1.90-1.80 (2H, m), 1.75-1.55 (1H, m), 1.50-1.20 (9H, m)

[2186] TABLE 229 >90% Example No. Purity (NMR) 1H NMR (δ) ppm

353 MS 634 (M + 1) 300 MHz, DMSO-d6 8.41 (1H, s), 8.33-8.29 (2H, m),8.16 (1H, d, J = 8. 2 Hz), 8.07 (1H, d, J = 8. 6 Hz), 7.77 (2H, d, J =8. 7H z), 7.62 (1H, d, J = 8. 0 Hz), 7.59-7.51 (4H, m), 7.28 (2H, d, J =8. 8 H z), 5.21 (2H, s), 4.56 (2H, s), 4. # 37 (1H, m), 2.40-2.18 (2H,m), 2. 15-1.95 (2H, m), 1.90-1.80 (2H, m), 1.75-1.55 (1H, m), 1.50-1.2 0(9H, m)

354 MS 664 (M + 1) 300 MHz, DMSO-d6 8.31 (1H, s), 8.25 (1H, d, J = 9. 0H z), 8.03 (1H, d, J = 8. 7 Hz), 7.76-7.71 (3H, m), 7.51-7.47 (5H, m),7.33 (1H, s), 7.23 (2H, d, J = 9. 0 H z), 5.14 (2H, s), 4.36 (1H, m), 4.02 (1H, m), 3.75 (1H, m), 3.56 (1H , m), 3.22 (2H, m), 2.40-2.18 (2H # ,m), 2.15-1.95 (2H, m), 1.90-1. 55 (5H, m), 1.50-1.20 (5H, m)

355 MS 624 (M + 1) 300 MHz, DMSO-d6 8.62 (1H, t, J = 5. 7 Hz), 8.32-8.30 (2H, m), 8.25 (1H, d, J = 3. 7 Hz), 8.03 (1H, d, J = 8. 7 Hz), 7.96(1H, d, J = 8. 1 Hz), 7.86 (1H, s), 7.75 ( 1H, d, J = 9. 0 Hz), 7.72(2H, d, J = 9 .0 Hz), 7.55-7.50 (4H, m), 7.22 ( 2H, d, J = 9. 0 Hz),5.17 (2H, s), 4. # 35 (1H, m), 3.52 (2H, t, J = 6. 0 Hz) , 3.36 (2H, t,J = 6. 0 Hz), 2.40-2. 18 (2H, m), 2.15-1.95 (2H, m), 1. 90-1.80 (2H, m),1.75-1.55 (1H, m), 1.50-1.20 (3H, m)

[2187] TABLE 230 >90% Example No. Purity (NMR) 1H NMR (δ) ppm

356 MS 671 (M + 1) 300 Mz, DMSO-d6 9.30 (1H, t, J = 5. 9 Hz), 8.54 (2H,d, J = 5. 9 Hz), 8.22 (1H, s), 8.02-7.79 (5H, m), 7.59and7.12 (4H, A Bq,J = 8. 6 Hz), 7.55 (4H, s), 7.37 (2H, d, J = 5. 9 Hz), 5.15 (2H, s), 4.54 (2H, d, J = 5. 7 Hz), 4.26 (1H, b rt, J = 12. 8 Hz), 2.36-2.18 (2H,b # rm), 1.97-1.78 (4H, brm), 1.70-1.60 (1H, brm), 1.47-1.17 (3H, b rm)

357 MS 608 (M + 1) 300 Mz, DMSO-d6 8.31 (1H, d, J = 1. 5 Hz), 8.43 (1H,d, J = 8. 4 Hz), 8.03 (1H, dd, J = 8. 4 , 1. 5 Hz), 7.74 (1H, d, J = 8.1 Hz), 7.73and7.23 (4H, ABq, J = 9. 0 Hz) 7.54-7.51 (5H, m), 7.37 (1H,d, J = 1. 8 Hz), 5.14 (2H, s), 4.36 (1H brt, J = 12. 1 Hz), 2.98 (6H,bms) # , 2.37-2.20 (2H, bm), 2.08-1.8 1 (4H, brm, 1.70-1.60 (1H, brm)1.50-1.21 (3H, brm)

358 MS 635 (M + 1) 300 MHz, DMSO-d6 8.33 (1H, s), 8.31 (1H, d, J = 8. 7H z), 8.14 (1H, s), 8.07 (1H, d, J = 8 .7 Hz), 7.92 (1H, d, J = 8. 0Hz), 7. 76 (2H, d, J = 8. 7 Hz), 7.52-7.40 ( 5H, m), 7.31-7.26 (3H, m),5.15 ( 2H, s), 4.37 (1H, m), 2.40-2.18 ( 2H, m), 2.15-1.95 (2H, m),1.90- # 1.80 (2H, m), 1.75-1.55 (1H, m), 1.50-1.20 (3H, m)

[2188] TABLE 231 >90% Example No. Purity (NMR) 1H NMR (δ) ppm

359 MS 700 (M + 1) 300 MHz, DMSO-d6 8.31 (1H, s), 8.25 (1H, d, J = 8. 7H z), 8.10-7.90 (2H, m), 7.82 (1H, dd, J = 7. 8 Hz, 1. 8 Hz), 7.72 (2H,d , J = 9. 0 Hz), 7.63 (1H, d, J = 8. 1 Hz ), 7.23 (2H, d, J = 9. 0 Hz),5.25 (2 H, s), 4.34 (1H, m), 3.65-3.50 (1 H, m), 3.20-3.05 (2H, m),2.90-2 # .75 (2H, m), 2.40-2.15 (2H, m), 2 .10-1.10 (12H, m)

360 MS 592 (M + 1) 300 MHz, DMSO-d6 8.33 (1H, s), 8.30 (1H, d, J = 8. 5H z), 8.06 (1H, d, J = 10. 1 Hz), 8.80 -8.65 (3H, m), 8.60-8.45 (3H, m), 7.42 (1H, d, J = 7. 8 Hz), 7.35-7. 15 (4H, m), 5.15 (2H, s), 4.36 (1H, m), 3.01, 2.97 (6H, s), 2.40-2. 15 (2H, m), 2.10-1.75 (4H, m), 1. #70-1.55 (1H, m), 1.50-1.20 (3H), m)

361 MS 592 (M + 1) 300 MHz, DMSO-d6 8.35-8.20 (2H, m), 8.05 (1H, d, J=8. 7 Hz), 8.80-8.65 (3H, m), 7.6 0-7.40 (3H, m), 7.40-7.30 (5H, m ),5.17 (2H, s), 4.35 (1H, m), 3.0 1, 2.97 (6H, s), 2.40-1.15 (2H, m ),2.10-1.80 (4H, m), 1.70-1.20 (4H, m)

[2189] TABLE 232 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

362 MS 614 (M + 1) 300 MHz, DMSO-d6 8.33 (1H, s), 8.29 (1H, d, J = 8. 7H z), 8.06 (1H, d, J = 8. 7 Hz) 7.79 ( 2H, d, J = 9. 0 Hz), 7.76 (1H, d,J = 9 . 0 Hz), 7.60 (1H, d, J = 8. 1 Hz), 7. 53 (1H, dd, J = 1. 7 Hz,8.0 Hz), 7.3 5 (2H, d, J = 8. 7 Hz), 6.85-6.80 (2 H, m) 5.29 (2H, s)4.38 (1H, m), # 3.01, 2.96 (6H, s), 2.40-2.18 (2 H, m), 2.15-1.95 (2H,m), 1.90-1 .80 (2H, m), 1.75-1.55 (1H, m), 1 .50-1.20 (3H, m)

363 MS 586 (M + 1) 300 MHz, DMSO-d6 8.28 (1H, d, J = 1. 3 Hz), 8.20-8.10 (2H, m), 8.98 (1H, d, J = 8. 6 Hz), 7.90-7.80 (2H, m), 7.75 (2H, d, J=8.7 Hz), 7.36 (2H, d, J = 8. 7 Hz), 7.04 (1H, d, J = 1. 3 Hz), 5.35(2H, s), 4.36 (1H, m), 2.39 (3H, s), 2. 35-2.15 # (2H, m), 2.05-1.75(4H, m), 1.70-1.60 (1H, m), 1.50-1.2 0 (3H, m)

364 MS 604 (M + 1) 300 MHz, DMSO-d6 8.31 (1H, s), 8.26 (1H, d, J = 8. 7H z), 8.13 (1H, s), 8.04 (1H, d, J = 9 . 0 Hz), 7.90-7.70 (4H, m), 7.65( 1H, s), 7.39 (2H, d, J = 9. 0 Hz), 5. 37 (2H, s), 4.38 (1H, m),2.40-2. 20 (2H, m), 2.15-2.00 (2H, m), 1. 95-1.80 (2H, m), # 1.75-1.60(1H, m), 1.50-1.20 (3H, m)

[2190] TABLE 233 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

365 MS 618 (M + 1) 300 MHz, DMSO-d6 8.28 (1H, s), 8.23 (1H, s), 8.17 (1H, d, J = 8. 7 Hz), 8.00 (2H, t, J = 6 . 9 Hz), 7.69 (2H, d, J = 8. 4Hz), 7. 60-7.45 (5H, m), 7.21 (2H, d, J = 8 . 4 Hz), 7.05 (1H, s) 5.19(2H, s), 4.33 (1H, m), 2.41 (3H, s), 2.40-2.20 (2H, m), 2.10-1.80 (4H,m), # 1.70-1.60 (1H, m), 1.50-1.20 (3 H, m)

366 MS 634 (M + 1) 300 MHz, DMSO-d6 8.26 (1H, s), 8.17 (1H, s, 8.11 (1H, d, J = 8. 7 Hz), 7.95 (2H, d, J = 9 . 6 Hz), 7.70-7.40 (8H, m), 7.19( 2H, d, J = 8. 4 Hz), 5.18 (2H, s), 4. 30 (1H, m), 2.51 (3H, s),2.40-2. 15 (2H, m), 2.05-1.80 (4H, m), 1. 75-1.60 (1H, m), 1.50-1.20(3H, m)

367 MS 605 (M + 1) 300 Mz, DMSO-d6 8.42 (1H, d, J = 1. 9 Hz), 8.30 (1H,J = , 1. 5 Hz), 8.27 (1H, d, J = 8. 7 Hz ), 8.18 (1H, dd, J = 7. 9, 1. 9Hz), 8 .04 (1H, dd, J = 8. 7, 1. 5 Hz), 7.75 and7.29 (4H, ABq, J = 8. 9Hz) 7.63 (1H, d, J = 7.9 Hz), 5.23 (2H, s), 4 . 36 (1H, brt, J = 12. 3Hz) 2.37-2. # 20 (2H, bm), 2.08-1.80 (4H, brm ), 1.71-1.60 (1H, brm),1.51-1. 21 (3H, bm)

[2191] TABLE 234 >90% Example No. Purity (NMR) 1H NMR (δ) ppm

368 MS 562 (M + 1) 300 Mz, DMSO-d6 8.30 (1H, d, J = 1. 5 Hz), 8.25 (1H,d, J = 8. 6 Hz), 8.04 (1H, dd, J = 8. 6 , 1.5 Hz), 7.93and7.67 (4H, ABq,J = 8. 1 Hz), 7.80 (1H, d, J = 2. 2 Hz) , 7.72and7.21 (4H, A′ B′ q, J =8. 6 Hz), 7.60 (1H, dd, J = 8. 1, 2. 2 Hz) # , 7.44 (1H, d, J = 8. 1Hz), 5.13 (2H , s), 4.34 (1H, brt, J = 11. 7 Hz), 2 .37-2.19 (2H, brm),2.09-1.80 ( 4H, brm), 1.72-1.60 (1H, brm), 1 .50-1.21 (3H, brm)

369 MS 605 (M + 1) 300 Mz, DMSO-d6 8.30 (1H, d, J = 1. 5 Hz), 8.25 (1H,d, J = 8. 6 Hz) 8.16and7.72 (4H, A Bq, J = 8. 4 Hz), 8.13 (1H, dd, J =8. 6, 1. 5 Hz), 7.80 (1Hd, J = 2. 2 Hz), 7.70and7.24 (4H, A′ B′ q, J =8. 8 H z), 7.61 (1H, dd, J = 8. 1, 2. 2 Hz), 7.48 (1H, d, J = 8. 1 Hz),5.17 (2H, # s), 4.33 (1H, brt, J = 12. 1 Hz), 2. 36-2.18 (2H, brm),2.08-1.77 (4 H, brm), 1.69-1.57 (1H, brm), 1. 49-1.17 (3H, brm)

370 MS 680 (M + 1) 300 MHz, DMSO-d6 10.94 (1H, brs), 8.33 (1H, s), 8. 27(1H, d, J = 8. 7 Hz), 8.04 (1H, d, J = 8. 7 Hz), 7.74 (2H, d, J = 8. 4Hz) , 7.56-7.29 (6H, m), 7.23 (2H, d, J = 8. 7 Hz), 7.13 (1H, d, J = 8.7 Hz) , 5.08 (2H, s), 4.51 (2H, brs), 4. 36 (1H, m), 3.94 (1H, brs),3.75- # 3.00 (6H, m), 3.20-1.20 (14H, m)

[2192] TABLE 235 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

371 MS 652 (M + 1) 300 MHz, DMSO-d6 8.31 (1H, d, J = 1. 5 Hz), 8.17 (1H,d, J = 9. 0 Hz), 7.99 (1H, dd, J = 8. 7 Hz, 1.4 Hz), 7.70-7.55 (2H, m),7 .50-7.30 (6H, m), 7.19 (1H, dd, J =12. 0 Hz, 2.2 Hz), 7.06 (1H, dd, J=8. 6 Hz, 2. 2 Hz), 5.08 (2H, 4.10 ( 1H, m), 3.68 (2H, brt, J = 5. 2),2. # 50 (2H, brt, J = 1. 8 Hz), 2.30-2.1 0 (2H, m), 2.00-1.75 (8H, m),1.7 0-1.55 (1H, m), 1.50-1.20 (3H, m )

372 MS 626 (M + 1) 300 Mz, DMSO-d6 8.29 (1H, d, J = 1.5 Hz), 8.11 (1H,d, J = 8. 6 Hz), 7.96 (1H, dd, J = 8. 6 , 1.5 Hz), 7.89 (1H, s) 7.78and7.56 (4H, ABq, J = 8.4 Hz), 7.69 (1H , s), 7.66 (1H, t, J = 8. 8 Hz),7.31 (1H, dd, J = 12. 1, 2. 2 Hz), 7.18 (1 H, dd, J = 8. 8, 2. 2 Hz),5.37 (2H, s # ), 4.08 (1H, brt, J = 11. 0 Hz), 3.0 2 (3H, s), 2.96 (3H,s), 2.31-2.1 4 (2H, bm), 1.95-1.77 (4H, brm, ) 1.69-1.59 (31H, brm),1.46-1. 18 (3H, brm)

373 MS 613 (M + 1) 300 MHz, DMSO-d6 11.40 (1H, brs), 9.25 (2H, brs),8.29 (1H, d, J = 1. 3 Hz), 8.12-8.0 9 (2H, m), 7.96 (1H, d, J = 4. 7Hz), 7.88 (1H, dd, J = 1. 8 Hz, 8. 1 Hz), 7 .67-7.63 (2H, m), 7.56 (2H,d, J =8.7 Hz), 7.51 (2H, d, J = 8. 7 Hz), 7 .17 (1H, d, J = 12. 0 Hz),7.05 (1H, # d, J = 8. 6 Hz), 5.16 (2H, s) ,4.05 ( 1H, m), 2.40-2.10 (2H,m), 2.00-1.75 (4H, m), 1.70-1.55 (1H, m), 1.50-1.20 (3H, m)

[2193] TABLE 236 >90% Example No. Purity (NMR) 1H NMR (δ) ppm

372 MS 639 (M + 1) 300 MHz, DMSO-d6 13.21 (1H, brs), 8.31 (1H, d, J = 1.4 Hz), 8.18-8.15 (2H, m), 7.99 ( 1H, d, J = 8. 7 Hz), 7.94 (1H, dd, J=1. 8 Hz, 8. 0 Hz), 7.70-7.53 (6H, m ), 7.17 (1H, d, J = 12. 0 Hz), 7.05( 1H, d, J = 8. 6 Hz), 5.20 (2H, s), 4. 09 (1H, m), 2.40-2.10 (2H, m),2. # 00-1.75 (4H, m), 1.70-1.55 (1H, m), 1.50-1.20 (3H, m)

375 MS 658 (M + 1) 300 MHz, DMSO-d6 8.32 (1H, d, J = 1. 5 Hz), 8.23 (1H,d, J = 1. 5 Hz), 8.19 (1H, d, J = 9. 0 H z), 8.03-7.98 (2H, m), 7.68(1H, t, J = 8. 4 Hz), 7.60 (1H, d, J = 8. 1 H z), 7.56 (2H, d, J = 9. 3Hz), 7.53 ( 2H, d, J = 9. 0 Hz), 7.22 (1H, dd, J =2. 1 Hz, 12. 0 Hz),7.09 (1H, dd, J = # 2.1 Hz, 8. 4 Hz), 5. 21 (2H, s), 4.1 2 (1H, m),2.40-2.10 (2H, m), 2.0 0-1.75 (4H, m), 1.70-1.55 (1H, m ), 1.50-1.20(3H, m)

376 MS 655 (M + 1) 300 MHz, DMSO-d6 13.61 (1H, brs), 8.34-8.30 (2H, m),8.21 (1H, d, J = 8.7 Hz), 8.07 ( 1H, dd, J = 1. 8 Hz, 8. 1 Hz), 8.02 (1H, dd, J = 1. 5 Hz, 8.7 Hz), 7.69 (1H , t, J = 8. 4 Hz), 7.57-7.49 (5H,m) , 7.22 (1H, dd, J = 2. 7 Hz, 12. 0 Hz) 7.09 (1H, dd, J = 2. 4 Hz, 9.0 Hz), # 5.19 (2H, s), 4.12 (1H, m), 2.40-2.10 (2H, m), 2.00-1.75 (4H,m), 1.70-1.55 (1H, m), 1.50-1.20 (3 H, m)

[2194] TABLE 237 >90% Example No. Purity (NMR) 1H NMR (δ) ppm

377 MS 638 (M + 1) 300 Mz, DMSO-d6 8.60 (1H, d, J = 4. 5 Hz), 8.29 (1H,d, J = 1. 5 Hz), 8.14 (1H, d, J = 8. 9 H z), 8.13 (1H, d, J = 1. 5 Hz),7.98 ( 1H, dd, J = 8. 9, 1. 5 Hz), 7.94 (1H, dd, J = 8. 1, 1. 5 Hz),7.64 (1H, t, J =8. 7 Hz), 7.52and7.49 (1H, ABq, J = 9. 0 Hz), 7.46 (1H,d, J = 8. 1 Hz) # , 7.18 (1H, dd, J = 12. 1,2. 3 Hz), 7 .05 (1H, dd, J =8. 7, 2. 3 Hz), 5.13 (2H, s), 4.08 (1H, brt, J = 12. 1H) , 2.95-2.84(1H, m), 2.31-2.14 ( 2H, brm), 1.97-1.78 (4H, bm), 1 .72-1.59 (1H, brm),1.47-1.21 ( 3H, brm), 0.76-0.58 (4H, m)

378 MS 652 (M + 1) 300 Mz, DMSO-d6 8.77 (1H, d, J = 1. 4 Hz), 8.30 (1H,d, J = 1. 4 Hz), 8.16 (1H, d, J = 1. 8 H z), 8.13 (1H, d, J = 8. 4 Hz),7.98 ( 2H, dd, J = 8. 4, 1. 8 Hz), 7.65 (1H, t, J = 8. 4 Hz),7.53and7.49 (4H, A Bq, J = 8. 8 Hz), 7.47 (1H, d, J = 7. 7 Hz), 7.18(1H, dd, J = 12. 1, 2. 2 Hz # ), 7.05 (1H, dd, J = 8. 4, 2. 2 Hz), 5 13(2H, s), 4.53-4.40 (1H, m), 4 .09 (1H, brt, J = 12. 8 Hz), 2.31-2 .02(6H, brt), 1.96-1.80 (4H, b rm), 1.78-1.60 (3H, brm), 1.47-1.21 (3H,brm)

379 MS 654 (M + 1) 300 Mz, DMSO-d6 8.29 (1H, d, J = 1. 1 Hz), 8.11 (1H,d, J = 1.5 Hz), 8.11 (1H, d, J = 8. 8 H z), 7.98-7.91 (2H, m), 7.89 (1H,s), 7.63 (1H, t, J = 8. 8 Hz), 7.52a nd7.48 (4H, ABq, J = 8. 6 Hz), 7.44(1H, d, J = 8. 1 Hz), 7.17 (1H, dd, J =12. 1, 2. 2 Hz), 7.04 (1H, dd, J= 8 # .8, 2. 2 Hz), 5.12 (2H, s), 4.07 (1 H, brt, J = 12. 4 Hz),2.33-2.14 (2 H, brm), 1.96-1.79 (4H, brm), 1. 70-1.60 (1H, brm),1.48-1.21 (3 H, brm), 1.41 (9H, s)

[2195] TABLE 238 >90% Example No. Purity (NMR) 1H NMR (δ) ppm

380 MS 654 (M + 1) 300 MHz, DMSO-d6 8.62 (1H, t, J = 5. 5 Hz), 8.30 (1H,d, J = 1. 5 Hz), 8.17 (1H, d, J = 1. 8 H z), 8.14 (1H, d, J = 8. 8 Hz),7.98 ( 1H, dd, J = 8. 1, 1. 8 Hz), 7.64 (1H, t, J = 8. 8 Hz),7.52and7.50 (4H, A Bq, J = 8. 8 Hz), 7.48 (1H, d, J = 8. 1 Hz), 7.18(1H, dd, J = 12. 1, # 2. 2 Hz ), 7.05 (1H, dd, J = 8. 8, 2. 2 Hz), 5 .14(2H, s), 4/08 (1H, brt, J = 12. 1 Hz), 3.13 (1H, t, J = 6. 2 Hz), 2.31-2.14 (2H, brm), 1.97-1.78 (5H , brm), 1.70-1.60 (1H, brm), 1.4 7-1.21(3H, brm), 0.92 (3H, s), 0 .90 (3H, s)

381 MS 656 (M + 1) 300 MHz, DMSO-d6 8.29 (1H, d, J = 1. 5 Hz), 8.27 (1H,d, J = 8. 3 Hz), 8.18 (1H, d, J = 1. 9H z), 8.13 (1H, d, J = 8. 7 Hz),8.01-7.96 (2H, m), 7.64 (1H, t, J = 8. 7 H z), 7.52and7.49 (1H, ABq, J =8. 8 Hz), 7.49 (1H, d, J = 7. 9 Hz), 7.18 (1H, dd, J = 12. 1, 2. 3 Hz),7.05 (1 # H, dd, J = 8. 7, 2. 3 Hz), 5.13 (2H, s ), 4.12-4.00 (2H, m),3.52-3.34 (2H, m), 2.31-2.14 (2H, brm), 1. 97-1.79 (4H, brm), 1.71-1.60(1 H, brm), 1.48-1.21 (3H, m), 1.17 and1.15 (total3H, each s)

382 MS 628 (M + 1) 300 MHZ, DMSO-d6 8.30 (1H, d, J = 1. 5 Hz), 8.13 (1H,d, J = 8. 8 Hz), 8.09 (1H, d, J = 1. 5 H z), 7.98 (1H, dd, J = 8. 8, 1.5 Hz), 7.86 (1H, dd, J = 8. 1, 1. 5 Hz), 7.6 4 (1H, J = 8. 8 Hz),7.55-7.47 (5H, m), 7.17 (1H, dd, J = 12. 1, 2. 2 Hz) , 7.05 (1H, dd, J =8. 8, 2. 2 Hz), 5. # 14 (2H, s), 4/08 (1H, brt, J = 12. 8 Hz), 3.75 (3H,s), 2.32-2.14 (2H , brm), 1.96-1.78 (4H, brm), 1.7 0-1.59 (1H, brm),1.47-1.21 (3H , brm)

[2196] TABLE 239 >90% Example No. Purity (NMR) 1H NMR (δ) ppm

383 MS 672 (M + 1) 300 MHz, DMSO-d6 8.57 (1H, t, J = 5. 5 Hz), 8.29 (1H,d, J = 1. 4 Hz), 8.19 (1H, d, J = 1. 5 H z), 8.12 (1H, d, J = 9. 2 Hz),8.01-7.95 (2H, m), 7.64 (1H, t, J = 8. 8 H z), 7.53and7.50 (4H, ABq, J =8. 8 Hz), 7.48 (1H, d, J = 7. 7 Hz), 7.17 (1H, dd, J = 12. 1, 2. 2 Hz),7.04 (1 # H, dd, J = 8. 8, 2. 2 Hz), 5.14 (2H, s ), 4/08 (1H, brt, J =13. 9 Hz), 3.7 0-3.66 (1H, m), 3.48-3.36 (3H, m ), 3.28-3.20 (1H, m),2.32-2.13 (2H, brm), 1.96-1.79 (4H, brm), 1.71-1.60 (1H, brm), 1.47-1.19(3H, brm)

384 MS 640 (M + 1) 300 MHz, DMSO-d6 8.30 (1H, d, J = 1. 5 Hz), 8.14 (1H,d, J = 8. 4 Hz), 7.98 (1H, dd, J = 8. 4 , 1. 5 Hz), 7.68 (1H, brs), 7.63(1 H, t, J = 8. 4 Hz), 7.51 (5H, s), 7.4 3 (1H, d, J = 8. 1 Hz), 7.17(1H, dd, J = 12. 5, 1. 8 Hz), 7.03 (1H, dd, J =8. 4, 1. 8 Hz), 4.08 (1H,brt, J = 11 # . 4 Hz), 3.50and3.30 (total2H, e ach brs), 2.97 (3H, brs),2.33-2.13 (2H, brm), 1.96-1.79 (4H, brm), 1.70-1.59 (1H, brm), 1.47-1.03(6H, brm),

385 MS 654 (M + 1) 300 MHz, DMSO-d6 8.29 (1H, d, J = 1. 5 Hz), 8.12 (1H,d, J = 8. 8 Hz), 7.97 (1H, dd, J = 8. 8 , 1. 5 Hz), 7.72-7.60 (2H, m),7. 5 5-7.42 (6H, m), 7.16 (1H, d, J = 11 . 7 Hz), 7.03 (1H, d, J = 8. 4Hz), 5. 15 (2H, s), 4.07 (1H, brt, J — 12. 5 Hz), 3.44and3.22(total2H,eac h # s), 2.97 (3H, brs), 2.32-2.13 (2 H, brm), 1.72-1.50 (3H,brm), 1. 47-1.23 (3H, brm), 0.93and0.72 (total3H, each brs)

[2197] TABLE 240 >90% Example No. Purity (NMR) 1H NMR (δ) ppm

386 MS 654 (M + 1) 300 Mz, DMSO-d6 8.29 (1H, d, J = 1. 5 Hz), 8.12 (1H,d, J = 8. 7 Hz), 7.97 (1H, dd, J = 8. 7 , 1. 5 Hz) 7.74-7.60 (2H, m),7.54 -7.42 (6H, m), 7.17 (1H, dd, J = 12 . 1, 2. 2 Hz), 7.02 (1H, dd, J= 8. 3, 2. 2 Hz), 5.15 (2H, s), 4/06 (1H, b rt, J = 12. 8 Hz), 3.92 (1H,brs), 2 # .85 (3H, brs), 2.32-2.14 (2H, br m), 1.96-1.79 (4H, brm),1.70-1 .59 (1H, brm), 1.46-1.07 (3H, br m), 1.15 (6H, brs)

387 MS 694 (M + 1) 300 Mz, DMSO-d6 8.31 (1H, s), 8.14and7.97 (2H, A Bq,J = 8. 7 Hz), 7.63 (1H, s), 7.63 (1H, t, J = 8. 7 Hz), 7.51-7.41 (6H ,m), 7.16 (1H, dd, J = 12. 1, 1. 9 Hz ), 7.02 (1H, dd, J = 8. 7, 1. 9Hz), 5 .16 (2H, s), 4.26 (2H, brs), 4.07 (1H, brt, J = 12. 1 Hz),2.32-2.14 (2H, brm), 1.97-1.78 (5H, brm) 1 # .70-1.15 (1H, brm), 1.24(3H, s) , 1.21 (3H, s)

388 MS 654 (M + 1) 300 MHz, DMSO-d6 8.58 (1H, m), 8.29 (1H, s),8.20-8.10 (2H, m), 8.05-7.90 (2H, m), 7.64 (1H > t, J = 8. 4 Hz),7.60-7.4 0 (5H, m), 7.15 (1H, d, J = 12. 3 Hz) , 7.04 (1H, d, J = 8. 4Hz), 5.13 (2H , 2), 4.08 (1H, m), 3.40-3.20 (2H , m), 2.35-2.10 (2H, m),2.00-1. 20 (12H, m), 0.91 (3H, t, J = # 6.9 Hz )

[2198] TABLE 241 >90% Example No. Purity (NMR) 1H NMR (δ) ppm

389 MS 640 (M + 1) 300 MHz, DMSO-d6 8.60 (1H, m), 8.29 (1H, m), 8.29(1H, s), 8.20-7.90 (4H, m), 7.64 (1H, t, J = 9. 0 Hz), 7.60-7.40 (5H,m), 7.17 (1H, d, J = 12. 0 Hz), 7.04 (1H, d, J = 8. 7 Hz), 5.13 (2H, s),4.80 (1H, m), 3.35-3.15 (2H, m), 2.30-2.05 (2H, m), 2.00-1.10 (10H, m),0.91 # (3H, t, J = 7. 5 Hz)

390 MS 626 (M + 1) 300 MHz, DMSO-d6 8.62 (1H, m), 8, 30 (1H, s),8.20-8.10 (2H, m), 8.05-7.90 (2H, m), 7.65 (1H, t, J = 8. 4 Hz),7.60-7.4 0 (5H, m), 7.18 (1H, d, J = 12. 0 Hz) , 7.05 (1H, d, J = 8. 4Hz), 5.14 (2H , s), 4.09 (1H, m), 3.40-3.20 (2H , m), 2.35-2.10 (2H, m),2.00-1. # 80 (4H, m), 1.75-1.60 (1H, m), 1. 45-1.20 (3H, m), 1.15 (3H,t, J = 7 .2 Hz)

391 MS 641 (M + 1) 400 NHz, DMSO-d6 8.54 (1H, s), 8.31 (1H, s), 8.19 (1H, d, J = 8. 6 Hz), 8.01 (1H, d, J = 8 .6 Hz), 7.81 (1H, d, J = 2. 1Hz), 7. 64 (1H, t, J = 8. 4 Hz), 7.61 (1H, dd , J = 2. 3 Hz, 8. 4 Hz),7.47 (2H, d, J =8. 6 Hz), 7.43 (2H, d, J = 8. 8 Hz), 7.25 (1H, d, J = 8.# 4 Hz), 7.17 (1H, dd, J = 2. 3 Hz, 12. 1 Hz), 7.05 (1H, dd, J = 2. 3Hz, 8. 6 Hz), 5.05 (2H, s ), 4.12 (1H, m), 2.96 (6H, s), 2.4 0-2.10 (2H,m), 2.00-1.75 (4H, m ), 1.70-1.55 (1H, m), 1.50-1.20 (3H, m)

[2199] TABLE 242 >90% Example No. Purity (NMR) 1H NMR (δ) ppm

392 MS 683 (M + 1) 300 MHz, DMSO-d6 8.79 (1H, s), 8.29 (1H, d, J = 1. 5H z), 8.13 (1H, d, J = 8. 8 Hz), 7.98 ( 1H, dd, J = 8. 8, 1. 5 Hz), 7.80(1H, d, J = 2. 2 Hz), 7.63 (1H, t, J = 8. 4 H z), 7.61 (1H, dd, J = 8.2, 2. 2 Hz), 7.47and7.43 (4H, ABq, J = 8. 8 Hz) , 7.26 (1H, d, J = 8. 2Hz), # 7.14 (1H , dd, J = 12. 1, 2. 2 Hz ), 7.02 (1H, d d, J = 8. 4, 2.2 Hz), 5.05 (2H, s), 4 .08 (1H, brt, J = 12. 1 Hz), 3.64-3 .61 (2H, m),3.48-3.45 (2H, m), 2 .32-2.13 (2H, brm), 1.96-1.78 ( 4H, brm), 1.70-1.66(1H, brm), 1 .44-1.19 (3H, brm)

393 MS 613 (M + 1) 400 MHz, DMSO-d6 8.94 (1H, s), 8.31 (1H, d, J = 1. 0H z), 8.18 (1H, d, J = 8. 6 Hz), 8.00 ( 1H, dd, J = 1. 4 Hz, 8. 8 Hz),7.71 (1 H, d, J = 2. 2 Hz), 7.66 (1H, t, J = 8. 6 Hz), 7.52 (1H, dd, J =2. 4 Hz, 8. 6 Hz), 7.46 (2H, d, J = 8. 6 Hz), 7.42 (2H, d, J = 8. 2 Hz),7.24 (1H, d, # J =8. 4 Hz), 7.16 (1H, d, J = 12. 1 Hz), 7.04 (1H, dd, J= 2. 4 Hz, 8. 8 Hz), 5 .05 (2H, s), 4.13 (1H, m), 2.40-2 .10 (2H, m),2.00-1.75 (4H, m), 1 .70-1.55 (1H, m), 1.50-1.20 (3H , m)

394 MS 641 (M + 1) 300 MHz, DMSO-d6 8.93 (1H, s), 8.31 (1H, d, J = 1. 4H z), 8.19 (1H, d, J = 8. 8 Hz), 8.01 ( 1H, d, J = 8. 7 Hz), 7.71 (1H,d, J = 2 . 2 Hz), 7.66 (1H, t, J = 8. 5 Hz), 7. 51 (1H, dd, J = 2. 2 Hz,8. 4 Hz), 7.4 6 (2H, d, J = 8. 6 Hz), 7.41 (2H, d, J =8. # 7 Hz), 7.23(1H, d, J = 8. 4 Hz), 7.16 (1H, d, J = 12. 2 Hz), 7.05 (1H , d, J = 8. 7Hz), 5.05 (2H, s), 4.13 (1H, m), 3.12 (2H, q, J = 7. 2 Hz), 2 .40-2.10(2H, m), 2.00-1.75 (4H , m), 1.70-1.60 (1H, m), 1.55-1. 20 (3H, m), 1.06(3H, t, J = J. 2 Hz)

[2200] TABLE 243 >90% Example No. Purity (NMR) 1H NMR (δ) ppm

395 MS 655 (M + 1) 300 MHz, DMSO-d6 8.83 (1H, s), 8.32 (1H, d, J = 1. 4H z), 8.21 (1H, d, J = 8. 8 Hz), 8.02 ( 1H, dd, J = 1. 4 Hz, 8. 7 Hz),7.71 (1 H, d, J = 2. 1 Hz), 7.68 (1H, t, J = 8. 6 Hz), 7.49 (1H, dd, J =2. 2 Hz, 8. 4 Hz), 7.46 (2H, d, J = 8. 4 Hz), 7.41 (2H, d, J = 8. 6 Hz),# 7.23 (1H, d, J =8. 4 Hz), 7.17 (1H, d, J = 12. 2 Hz), 7.06 (1H, d, J =8. 7 Hz), 6.30 (1H, brs), 5.05 (2H, s), 4.14 (1H, m), 3.77 (1H, sept, J= 6. 5 Hz), 2.40-2.10 (2H, m), 2.00-1.75 (4H, m), 1.70-1.55 (1H, m),1.50-1.20 (3 H, m), 1.11 (6H, d, J = 6. 5 Hz)

396 MS 642 (M + 1) 300 MHz, DMSO-d6 8.37 (1H, d, J = 7. 3 Hz), 8.25 (1H,s), 8.15 (1H, s), 7.97 (2H, d, J = 8 . 8 Hz), 7.88 (1H, d, J = 8. 8 Hz),7. 58-7.47 (4H, m), 7.31 (1H, m), 7. 11 (1H, dd, J = 8. 4, 2. 2 Hz),6.98 ( 1H, dd, J = 8. 4, 2. 2), 5.13 (2H, s) , 4.13 (1H, q, J = 6. 6Hz), 3.98 (1H , # m), 2.19 (2H, m), 1.86 (4H, m) 1. 62 (1H, m) 1.31 (3H,m), 1.20 (6H, d, J = 6. 6 Hz)

397 MS 642 (M + 1) 300 MHz, DMSO-d6 8.40 (1H, d, J = 7. 9 Hz), 8.28 (1H,d, J = 1. 9 Hz), 8.15 (1H, d, J = 1. 9 H z), 8.11 (1H, d, J = 8. 7 Hz),7.96 ( 2H, m), 7.56 (1H, t, J = 8. 7 Hz), 7. 45 (3H, m), 7.18 (1H, m),7.08 (1H , dd, J = 12. 1, 1. 9 Hz), 6.96 (1H, d d, J = 8. 3, 2. 3 Hz),5.09 (2H, s), # 4 .14 (1H, m), 4.04 (1H, m), 2.23 (2 H, m), 1.86 (3H,m), 1.62 (1H, m), 1.33 (3H, m), 1.20 (6H, d, J = 6. 4 Hz)

[2201] TABLE 244 >90% Example No. Purity (NMR) 1H NMR (δ) ppm

398 MS 674 (M + 1) 8.41 (1H, d, J = 8. 1 Hz), 8.29 (1H, d, J = 1. 5 Hz),8.17 (1H, d, J = 1. 8 H z), 8.12 (1H, d, J = 8. 4 Hz), 8.01-7.95 (2H,m), 7.67-7.62 (2H, m), 7.55-7.51 (3H, m), 7.19 (1H, dd, J = 12. 1, 2. 2Hz), 7.05 (1H, dd, J =8. 8, 2. 2 Hz), 5.13 (2H, s), 4.10-4.00 (2H, m), #2.32-2.13 (4H, m), 1.71-1.60 (1H, m), 1.49-1.14 (3 H, m), 1.21 (3H, s),1.19 (3H, s)

399 MS 658 (M + 1) 300 Mz, DMSO-d6 8.39 (1H, d, J = 7. 7 Hz), 8.29 (1H,d, J = 1. 5 Hz) 8.16 (1H, d, J = 1. 8 H z), 8.11 (1H, d, J = 8. 8 Hz),8.00-7.95 (2H, m), 7.69-7.61 (2H, m), 7.54-7.46 (3H, m), 7.18 (1H, dd, J= 12. 1, 2. 2 Hz), 7.04 (1H, dd, J =8. 8, 2. 2 Hz), 5.13 (2H, s), 4.20-# 4.02 (2H, m), 2.33-2.13 (2H, brm ), 1.97-1.80 (4H, m), 1.72-1.61 (1H,m), 1.44-1.13 (3H, m), 1.21 (3H, s), 1.19 (3H, s)

400 MS 642 (M + 1) 300 MHz, DMSO-d6 8.39 (1H, d, J = 7. 7 Hz), 8.29 (1H,s), 8.17 (1H, d, J = 1. 5 Hz), 8.11 (1H, d, J = 8. 8 Hz), 7.98 (2H, m),7.73 ( 2H, m), 7.64 (1H, t, J = 8. 4 Hz), 7.52 (1H, d, J = 8. 0 Hz),7.46 (1H, dd, J = 8. 4, 1. 8 Hz), 7.18 (1H, dd, J = 11. 9, 2. 0 Hz),7.05 (1H, dd, # J =8. 6, 2. 4 Hz), 5.14 (2H, s), 4.13 ( 2H, m), 2.22(2H, m), 1.88 (4H, m) 1.64 (1H, m), 1.34 (3H, m), 1.20 ( 6H, d, J = 6.6Hz)

[2202] TABLE 245 >90% Example No. Purity (NMR) 1H NMR (δ) ppm

401 MS 658 (M + 1) 300 MHz, DMSO-d6 8.38 (1H, d, J = 7. 8 Hz), 8.28 (1H,s), 8.20-8.05 (2H, m), 8.00-7.9 0 (2H, m), 7.66-7.30 (5H, m), 7.0 9 (1H,d, J = 12. 3 Hz), 6.97 (1H, d, J = 10. 2 Hz), 5/09 (2H, s), 4.20-4 .00(2H, m), 2.30-2.10 (2H, m), 2 .00-1.80 (4H, m), 1.70-1.60 (1H , m), #1.40-1.10 (3H, m), 1.19 (6H , d, J = 6. 6 Hz)

402 MS 670 (M + 1) 300 Mz, DMSO-d6 8.25 (1H, s), 8.03 (1H, d, J = 8. 7 Hz), 7.91 (1H, d, J = 8. 7 Hz), 7.83 ( 1H, s), 7.70-7.35 (6H, m), 7.04 (1H, d, J = 12. 0 Hz), 6.93 (1H, d, J =8. 4 Hz), 5.09 (2H, s), 4.00 (1H,m ), 3.60-3.40 (4H, m), 2.30-2.10 (2H, m), 1.45-1.15 (3H, m)

403 MS 670 (M + 1) 400 MHz, DMSO-d6 8.25 (1H, s), 8.08 (1H, d, J = 8. 4H z), 7.92 (1H, d, J = 9. 2 Hz), 7.79 ( 1H, s), 7.66-7.49 (4H, m), 7.42( 1H, d, J = 7. 6 Hz), 7.31-7.28 (1H, m), 7.14 (1H, d, J = 11. 3 Hz),6.99 (1H, d, J = 8. 8 Hz), 5.12 (2H, s), 4 .012 (1H, m), 3.54-3.33 #(4H, m), 2 .29-2.08 (2H, m), 1.93-1.73 (8H , m), 1.67-1.52 (1H, m),1.48-1. 11 (3H, m)

[2203] TABLE 246 >90% Example No. Purity (NMR) 1H NMR (δ) ppm

404 MS 658 (M + 1) 400 MHz, DMSO-d6 8.41 (1H, d, J = 7. 6 Hz), 8.32 (1H,d, J = 1. 5 Hz), 8.20 (1H, d, J = 8. 6 H z), 8.17 (1H, d, J = 1. 7 Hz),8.00 ( 1H, dt, J = 8. 8 Hz, 1. 5 Hz), 7.71-7 .64 (2H, m), 7.54 (1H, dd,J = 10. 3 Hz, 1. 9 Hz), 7.32 (1H, dd, J = 8. 2 H z, 1. 9 Hz), 7.22 (1H,# dd, J = 12. 1 H z, 2. 3 Hz), 7.08 (1H, dd, J = 8. 6 Hz ), 2. 3 Hz),5.17 (2H, s), 4.15 (1H , m), 2.31-2.14 (2H, m), 1.99-1. 70 (4H, m),1.70-1.60 (1H, m), 1. 46-1.20 (3H, m), 1.19 (6H, d, J = 6 . 6 Hz)

405 MS 650 (M + 1) 300 MHz, DMSO-d6 8.32 (1H, s), 8.19 (1H, d, J = 9. 0H z), 8.03-7.98 (2H, m), 7.75 (1H, dd, J = 2. 1 Hz, 8. 4 Hz), 7.67 (1H,t , J = 8. 6 Hz), 740-7.36 (3H, m), 7 .32 (2H, d, J = 8. 4 Hz), 7.19(1H, d d, J = 2. 1 Hz, 12. 3 Hz), 7.07 (1H, d d, J = 2. 1 Hz, 8. 7 Hz),# 5.11 (2H, s) , 4.12 (1H, m), 4.12 (1H, m), 3.90 (2H, t, J = 6. 9 Hz),2.54 (2H, t, J =8. 1 Hz), 2.50 (3H, s), 2.40-2.05 (4H, m), 2.00-1.75(4H, m), 1.70 -1.55 (1H, m), 1.50-1.20 (3H, m)

406 MS 652 (M + 1) 300 MHz, DMSO-d6 8.34 (1H, d, J = 7. 7 Hz), 8.29 (1H,s), 8.15 (1H, s), 8.11 ( 1H, d, J = 8. 8 Hz), 7.97 (2H, d, J = 9 . 2Hz), 7.63 (1H, t, J = 8. 8 Hz), 7. 47-7.31 (5H, m), 7.18 (1H, dd, J =12.4, 2. 2 Hz), 7.06 (1H, dd, J = 12 . 4, 2. 2 Hz), 5.13 (2H, s), 4.13 (2 #H, m), 1.96 (2H, m), 1.87 (4H, m), 1.62 (1H, m), 1.34 (3H, m), 1.20 (6H, d, J = 6. 2 Hz)

[2204] TABLE 247 >90% Example No. Purity (NMR) 1H NMR (δ) ppm

407 MS 708 (M + 1) 400 Mz, DMSO-d6 8.32 (1H, d, J = 1. 4 Hz), 8.20 (1H,d, J = 8. 8 Hz), 8.01 (1H, dd, J = 1. 6 Hz, 8. 8 Hz), 7.90 (1H, s), 7.67(1 H, t, J = 8. 4 Hz), 7.61 (1H, s), 7.5 5-7.50 (4H, m), 7.21 (1H, dd, J= 2 .3 Hz, 12.0 Hz), 7.06 (1H, dd, J = 2 .2 Hz, 8. 7 Hz), 5.10 (2H, #s), 4.11 (1H, m), 3.78 (2H, t, J = 6. 7 Hz), 3 .47 (2H, t, J = 7. 4 Hz),2.54-2.48 (2H, m), 2.40-2.10 (2H, m), 2.00 -1.80 (4H, m), 1.75-1.55 (1H,m) , 1.50-1.20 (3H, m)

408 MS 672 (M + 1) 400 Mz, DMSO-d6 8.32 (1H, d, J = 1. 6 Hz), 8.21 (1H,d, J = 8. 8 Hz), 8.02 (1H, dd, J = 1. 6 Hz, 8. 8 Hz), 7.76 (1H, s), 7.68(1 H, t, J = 8. 5 Hz), 7.59 (1H, s), 7.5 4-7.51 (4H, m), 7.21 (1H, dd, J= 2 .4 Hz, 12. 1 Hz), 7.07 (1H, dd, J = 2 .4 Hz, 8. 8 Hz), # 5.08 (2H,s), 4.11 (1H, m), 3.77 (2H, t, J = 6. 9 Hz), 2 .47 (2H, t, J = 8. 0 Hz),2.40-2.10 (4H, m), 2.00-1.80 (4H, m), 1.70 -1.60 (1H, m), 1.45-1.20 (3H,m)

409 MS 676 (M + 1) 300 Mz, DMSO-d68.28 (1H, d, J = 1 .5 Hz), 8.20-8.85(4H, m), 7.75 ( 1H, d, J = 6. 9 Hz), 7.70-7.45 (6H, m), 7.13 (1H, dd, J= 12. 0 Hz, 2.1 H z), 7.00 (1H, dd, J = 8. 7 Hz), 2. 1 H z), 5.22 (2H,s), 4.05 (1H, m), 3. 40-3.20 (1H, m), 2.30-2.10 (2H, m), 2.00- # 1.55(5H, m), 1.45-1.1 0 (3H, m), 1.00 (6H, d, J = 6. 6 Hz)

[2205] TABLE 248 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

410 MS 612 (M + 1) 300 MHz, DMSO-d6 8.31(1H, s), 8.00(1H, d, J=8.7Hz),7.88(1H, d, J=8.7Hz), 7.70 (1H, s), 7.65(1H, t, J=8.4Hz), 7.53(2H, d,J=8.4Hz), 7.49(2H, d, J=8.7Hz), 7.45-7.41(2H, m), 7.16(1H, d, J=12.0Hz),7.04(1H, d, J=8.7Hz), 5.14(2H, s), 4.68 (1H, quint, J=8.4Hz), 3.02,2.98(6H, s), 2.30-1.85(6H, m), 1.80-1.50(2H, m)

411 MS 668 (M + 1) 300 MHz, DMSO-d6 8.30(1H, s), 7.99(1H, d, J=9.0Hz),7.87(1H, d, J=8.7Hz), 7.67 (1H, s), 7.64(1H, t, J=8.1Hz), 7.53(2H, d,J=8.7Hz), 7.49(2H, d, J=7.5Hz), 7.45-7.41(2H, m), 7.15(1H, d, J=12.3Hz),7.02(1H, d, J=8.4Hz), 5.15(2H, s)4.67(1H, quint, J=8.7Hz), 4.02(1H, m),3.76 (1H, m), 3.55(1H, m), 3.22 (2H, m), 2.40-1.20(12H, m)

412 MS 626 (M + 1) 300 MHz, DMSO-d6 8.38(1H, d, J=7.5Hz), 8.33(1H, s),8.16(1H, s), 8.02(1H, d, J=8.7Hz), 7.98 (1H, d, J=9.0Hz), 7.91(1H, d,J=8.4Hz), 7.67(1H, t, J=8.4Hz), 7.53(2H, d, J=8.7Hz), 7.48(2H, d,J=8.7Hz), 7.46(1H, d, J=8.1Hz), 7.18(1H, d, J=11.7Hz), 7.06(1H, d,J=8.7Hz), 5.13(2H, s), 4.70(1H, quint, J=8.4Hz), 4.13(1H, sept,J=6.6Hz), 2.30-1.85(6H, m), 1.80-1.50(2H, m), #1.16(6H, d, J=6.3Hz)

[2206] TABLE 249 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

413 MS 608 (M + 1) 300 Mz, DMSO-d6 8.39(1H, d, J=7.5Hz), 8.31(1H, d,J=1.5Hz), 8.16(1H, d, J=1.9Hz), 8.06(1H, dd, J=8.8, 1.5Hz),7.99-7.95(2H, m), 7.76and7.24 (4H, ABq, J=8.9Hz), 7.53and7.50 (4H,A′B′q, J=9.1Hz), 7.46(1H, d, J=8.3Hz), 5.14(2H, s), 4.94 (1H, quint,J=9.0Hz), 4.19-4.08 (1H, m), 2.32-2.11(4H, brm), 2.10-1.95(2H, brm),1.78-1.62 (2H, brm), 1.26(3H, s), 1.18(3H, s)

414 MS 594 (M + 1) 300 Mz, DMSO-d6 8.31(1H, d, J=1.5Hz), 8.06(1H, dd,J=8.7, 1.5Hz), 7.97(1H, d, J=8.7Hz), 7.75and7.22(4H, ABq, J=8.9Hz),7.70(1H, d, J=1.9Hz), 7.53(1H, dd, J=7.9, 1.9Hz), 7.52(4H, s), 7.43(1H,d, J=7.9Hz), 5.15(2H, s), 4.93(1H, quint, J=8.9Hz), 3.01(3H, s),2.97(3H, s), 2.32-2.11(4H, brm), 2.09-1.94(2H, brm), 1.77-1.62(2H, brm)

415 MS 650 (M + 1) 300 Mz, DMSO-d6 8.31(1H, d, J=1.5Hz), 8.06(1H, dd,J=8.7, 1.5Hz), 7.98(1H, d, J=8.7Hz), 7.75and7.22(4H, ABq, J=8.9Hz),7.67(1H, d, J=1.5Hz), 7.52(4H, s), 7.49(1H, dd, J=7.9, 1.5Hz), 7.43(1H,d, J=8.9Hz), 5.16(2H, s), 4.93(1H, quint, J=8.9Hz), 3.76(1H, brs),3.55(2H, brs), 3.22 (2H, brs), 2.31-2.11(4H, brm), 2.16-1.95(2H, brm),1.88-1.62 (4H, brm), 1.48-1.28(2H, brm)

[2207] TABLE 250 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

416 MS 640 (M + 1) 300 MHz, DMSO-d6 8.38(1H, d, J=7.7Hz), 8.30(1H, s),8.20-7.90(4H, m), 7.72(2H, d, J=8.7Hz), 7.60-7.40(5H, m), 7.22(2H, d,J=8.7Hz), 5.13(2H, s), 4.47(1H, m), 4.15(1H, m), 2.90-2.70 (4H, m),2.60-2.30(4H, m), 1.19(6H, d, J=6.5Hz)

417 MS 652 (M + 1) 400 MHz, DMSO-d6 8.33(1H, s), 8.17(1H, d, J=8.6Hz),8.10(1H, d, J=8.6Hz), 7.82(1H, d, J=1.4Hz), 7.74(2H, d, J=8.7Hz),7.64(1H, dd, J=8.0Hz, 1.7Hz), 7.55-7.50(4H, m), 7.43 (1H, d, J=7.8Hz),7.24(1H, d, J=8.7Hz), 5.16(2H, s), 4.49(1H, m), 3.60-3.40 (4H, m),2.90-2.70 (4H, m), 2.60-2.30(4H, m), 2.20-1.80(4H, m)

418 MS 658 (M + 1) 400 MHz, DMSO-d6 8.34(1H, d, J=7.6Hz), 8.25(1H, s),8.11(1H, d, J=1.3Hz), 7.90-8.00(3H, m), 7.59(1H, t, J=8.6Hz),7.40-7.55(5H, m), 7.12(1H, d, J=11.9Hz), 7.00(1H, d, J=8.6Hz), 5.08(2H,s), 4.30-4.10(2H, m), 2.80-2.65(4H, m), 2.45-2.30 (2H, m), 1.15(6H, d,J=4.8Hz)

[2208] TABLE 251 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

419 MS 656 (M + 1) 400 MHz, DMSO-d6 8.30(1H, s), 8.05-7.95(3H, m),7.80-7.75(1H, m), 7.63(1H, t, J=8.6Hz), 7.55-7.35(5H, m), 7.15 (1H, dd,J=12.1Hz, 2.1Hz), 7.03 (1H, dd, J=8.7Hz, 2.3Hz), 5.10 (2H, s), 4.23(1H,m), 3.90(2H, t, J=7.0Hz), 2.95-2.70(4H, m), 2.60-2.35 (4H, m),2.30-2.00(4H, m)

420 MS 641 (M + 1) 300 Mz, DMSO-d6 8.37(1H, d, J=7.5Hz), 8.28(1H, d,J=1.5Hz), 8.17(1H, d, J=1.5Hz), 8.13(1H, d, J=8.7Hz), 7.97 (1H, dd,J=8.1, 1.5Hz), 7.94(1H, dd, J=8.7, 1.5Hz), 7.61(1H, t, J=8.7Hz),7.51and7.49(4H, ABq, J=8.9Hz), 7.46(1H, d, J=8.1Hz), 7.08(1H, dd,J=12.4, 2.3Hz), 6.97(1H, dd, J=8.7, 2.3Hz), 5.10 (2H, s), 4.20-4.08(1H,m), 3.62-3.56(2H, #brm), 3.13-3.10(2H, brm), 1.79-1.60(3H, brm),1.54-1.34(3H, brm), 1.21(3H, s), 1.18(3H, s)

421 MS 653 (M + 1) 300 Mz, DMSO-d6 8.24(1H, d, J=1.5Hz), 8.02(1H, d,J=8.7Hz), 7.88(1H, dd, J=8.7, 1.5Hz), 7.82(1H, d, J=1.9Hz), 7.63(1H, dd,J=7.9, 1.9Hz), 7.54 (1H, t, J=8.7Hz), 7.50(4H, s), 7.42(1H, d, J=7.9Hz),7.01(1H, # dd, J=12.0, 2.3Hz), 6.91(1H, dd, J=8.7, 2.3Hz), 5.11(2H, s),3.63-3.41(6H, m), 3.07-3.04(2H, brm), 1.95-1.79(4H, brm), 1.77-1.57(3H,brm), 1.50-1.32(3H, brm)

[2209] TABLE 252 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

422 MS 623 (M + 1) 300 MHz, DMSO-d6 10.99(2H, s), 8.44(1H, s), 8.30 (1H,s), 8.18(1H, d, J=8.7Hz), 8.14 (1H, d, J=8.7Hz), 7.98(1H, d, J=9.0Hz),7.70-7.66(2H, m), 7.57(2H, d, J=8.7Hz), 7.54(2H, d, J=8.7Hz), 7.21(1H,d, J=12.0Hz), 7.09(1H, d, J=8.4Hz), 5.19(2H, s), 4.05(4H, s),2.40-2.18(2H, m), 2.15-1.80(4H, m), 1.75-1.55(1H, m), 1.50-1.20(3H, m)

423 MS 640 (M + 1) 300 MHz, DMSO-d6 8.27(1H, s), 8.05(1H, d, J=8.7Hz),7.93 (1H, d, J=8.7Hz), 7.90(1H, s), 7.70(1H, d, J=8.4Hz), 7.59(1H, t,J=8.4Hz), 7.50(2H, d, J=9.0Hz), 7.45(2H, d, J=8.7Hz), 7.41(1H, d,J=8.4Hz), 7.12(1H, # d, J=12.0Hz)7.00(1H, d, J=8.7Hz), 5.10(2H, s),4.49(2H, t, J=7.8Hz), 4.14(2H, t, J=8.0Hz), 4.04(1H, m), 2.40-2.10(2H,m), 2.00-1.50(5H, m), 1.45-1.20(3H, m)

424 MS 639 (M + 1) 300 MHz, DMSO-d6 8.30(1H, s), 8.14(1H, d, J=8.4 Hz),7.98(1H, d, J=9.3Hz), 7.89(1H, s), 7.68(1H, d, J=8.4Hz), 7.62(1H, d,J=9.0Hz), 7.48(2H, d, J=8.4Hz), 7.43(2H, d, J=8.4Hz), 7.33(1H, d,J=8.4Hz), 7.16(1H, # d, J=12.0Hz), 7.04(1H, d, J=9.0Hz), 5.07(2H, s),4.10(1H, m), 3.92(2H, t, J=8.0Hz), 3.45(2H, t, J=8.0Hz), 2.40-2.10(2H,m), 2.00-1.50(5H, m), 1.45-1.20(3H, m)

[2210] TABLE 253 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

425 MS 639 (M + 1) 300 MHz, DMSO-d6 9.05(1H, s), 8.30(1H, s), 8.16 (1H,d, J=8.8Hz), 7.99(1H, d, J=8.6Hz), 7.72(1H, s), 7.64(1H, t, J=8.6Hz),7.52(1H, d, J=8.4Hz), 7.47(2H, d, J=8.7 #Hz), 7.42(2H d, J=8.6Hz),7.25(1H, d, J=8.4Hz), 7.15(1H, d, J=12.2Hz), 7.04 (1H, d, J=8.6Hz),6.60(1H, brs), 5.05(2H, s), 4.10(1H, m), 3.68 (2H, t, J=6.1Hz), 3.45(2H,t, J=6.1Hz), 2.40-2.10(2H, m), 2.00-1.55(5H, m), 1.50-1.20(3H, m)

426 MS 643 (M + 1) 300 MHz, DMSO-d6 8.32(1H, s), 8.24(1H, d, J=8.7Hz),8.03(1H, d, J=8.7Hz), 7.78-7.73(4H, m), 7.38-7.32(4H, m), 5.52(2H, s),4.88(2H, s), 4.40(2H, s), 4.37(1H, m), 2.92, 2.84(6H, s), 2.40-2.18(2H,m), 2.15-1.95(2H, m), 1.90-1.80(2H, m), 1.75-1.55(1H, m), 1.50-1.20(3H,m)

427 MS 641 (M + 1) 300 MHz, DMSO-d6 11.26(1H, brs), 8.35(1H, s),8.27(1H, d, J=9.0Hz), 8.05(1H, d, J=8.4Hz), 7.83-7.78(4H, m), 7.42-7.35(4H, m), 5.57(2H, s), 4.77, 4.73(2H, s), 4.37 (1H, m), 3.95 (1H, s),3.70-3.00(4H, m), 2.40-1.00(14H, m)

[2211] TABLE 254 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

428 MS 615 (M + 1) 300 MHz, DMSO-d6 8.31(1H, s), 8.26(1H, d J=9.0Hz),8.04(1H, d, J=8.7Hz), 7.79-7.73(4H, m), 7.38-7.31(6H, m), 5.53(2H, s),4.90(2H, s), 4.37 (1H, m), 4.05(2H, s), 2.40-2.18 (2H, m), 2.15-1.95(2H,m), 1.90-1.80(2H, m), 1.75-1.55(1H, m), 1.50-1.20(3H, m)

429 MS 603 (M + 1) 300 MHz, DMSO-d6 8.88(1H, q, J=4.5Hz), 8.33(1H, d,J=1.5Hz), 8.18(1H, d, J=8.7Hz), 8.01(1H, dd, J=1.5Hz, 8.7Hz),7.89-7.83(2H, m), 7.50-7.34 (3H, m), 7.20(1H, dd, J=2.1Hz, 8.4Hz),5.61(2H, s), 4.13(1H, m), 2.84(3H, d, J=4.8Hz), 2.40-2.10(2H, m),2.00-1.75(4H, m), 1.70-1.55(1H, m), 1.50-1.20(3H, m)

430 MS 633 (M + 1) 400 MHz, DMSO-d6 8.79(1H, t, J=5.9Hz), 8.31(1H, s),8.15(1H, d, J=8.7Hz), 7.99 (1H, d, J=8.8Hz), 7.87(1H, d, J=8.1Hz),7.85(1H, d, J=8.7Hz), 7.70(1H, t, J=8.4Hz), 7.42-7.33 (3H, m), 7.18(1H,d, J=8.8Hz), 5.60 (2H, s), 4.11(1H, m), 3.62-3.54(4H, m), 2.40-2.10(2H,m), 2.00-1.75(4H, m), 1.70-1.55 (1H, m), 1.50-1.20(3H, m)

[2212] TABLE 255 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

431 MS 616 (M + 1) 300 MHz, DMSO-d6 8.31(1H, s), 8.16(1H, d, J=8.8Hz),7.99(1H, d, J=8.7Hz), 7.74-7.60(4H, m), 7.37(2H, t, J=8.8Hz), 7.28(1H,dd, J=2.2Hz, 12.2Hz), 7.14(1H, dd, J=2.2Hz, 8.6Hz), 5.17(2H, s),4.10(1H, m), 3.15(6H, brs), 2.40-2.10(2H, m), 2.00-1.75(4H, m),1.70-1.55(1H, m), 1.50-1.15(3H, m)

432 MS 630 (M + 1) 300 MHz, DMSO-d6 8.45(1H, d, J=7.7Hz), 8.32(1H, s),8.19(1H, d, J=8.8Hz), 8.02-7.99(2H, m), 7.70(1H, t, J=8.6Hz), 7.60(2H,dd, J=5.4Hz, 8.7Hz), 7.37 (2H, t, J=8.8Hz), 7.27(1H, dd, J=2.3Hz,12.2Hz), 7.14(1H, dd, J=2.2Hz, 8.7 Hz), 5.16 (2H, s), 4.20-4.00(2H, m),2.40-2.10(2H, m), 2.00-1.75(4H, m), 1.70-1.55(1H, m), 1.50-1.20 (3H, m),1.18(6H, d, J=6.6Hz)

433 MS 672 (M + 1) 300 MHz, DMSO-d6 8.31(1H, d, J=1.4Hz), 8.15(1H, d,J=8.8Hz), 7.98(1H, dd, J=1.4Hz, 8.7Hz), 7.68-7.60(4H, m), 7.36 (2H, t,J=8.8Hz), 7.28(1H, dd, J=2.2Hz, 12.2Hz), 7.15(1H, dd, J=2.2Hz, 8.6Hz),5.17(2H, s), 4.10 (1H, m), 4.05-3.90(2H, m), 3.85-3.70 (1H, m),3.55-3.25(2H, m), 2.40-2.10 (2H, m), 2.00-1.75(6H, m), 1.70-1.55(1H, m),1.50-1.20(5H, m)

[2213] TABLE 256 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

434 MS 650 (M + 1) 300 Mz, DMSO-d6 8.45(1H, d, J=1.5Hz), 8.26 (1H, d,J=8.8Hz), 8.10(1H, dd, J=8.8, 1.5Hz), 7.72(1H, d, J=1.5Hz), 7.64(1H, t,J=8.6Hz), 7.56-7.48(5H, m), 7.44(1H, d, J=J=7.7Hz), 7.18(1H, dd, J=12.3,2.4Hz), 7.04(1H, dd, J=8.6, 2.4Hz), 5.15(2H, s), 4.08(1H, brt,J=11.7Hz), 3.02(3H, s), 2.99 (3H, s), 2.34-2.17(2H, brm), 1.97-1.81(4H,brm), 1.70-1.60 # (1H, brm), 1.49-1.21(3H, brm)

435 MS 623 (M + 1) 300 Mz, DMSO-d6 8.42(1H, d, J=1.5Hz), 8.24(1H, d,J=8.8Hz), 8.08(1H, dd, J=8.8, 1.5Hz), 8.00(2H, d, J=8.8Hz), 7.79(1H, d,J=7.8Hz), 7.62(1H, t, J=8.4Hz), 7.61-7.55(3H,), 7.44(1H, d, J=8.1Hz),7.16(1H, dd, J=12.1, 2.6Hz), 7.02(1H, dd, J=8.4, 2.6Hz), 5.12(2H, s),4.07(1H, brt, J=12.5Hz), 2.33(2H, brm), 1.96-1.79(4H, brm),1.71-1.61(1H, brm), 1.49-1.21(3H, brm)

436 MS 680 (M + 1) 300 MHz, DMSO-d6 8.41(1H, d, J=7.7Hz), 8.30-8.26 (2H,m), 8.18(1H, d, J=4.4 Hz), 7.99(1H, dd, J=1.7Hz, 8.0Hz), 7.89(1H, d,J=10.1Hz), 7.67(1H, t, J=8.8Hz), 7.55-7.45(5H, m), # 7.20(1H, d,J=12.2Hz), 7.07(1H, dd, J=2.1Hz, 8.7Hz), 5.14(2H, s), 4.18-4.11(2H, m),2.40-2.10 (2H, m), 2.00-1.75(4H, m), 1.70-1.55 (1H, m), 1.50-1.20(3H,m), 1.20(6H, d, J=6.6Hz)

[2214] TABLE 257 Example No. Purity >90% (NMR) 1H NMR (δ) ppm

437 MS 580 (M + 1)

438 MS 607 (M + 1)

439 MS 591 (M + 1) 300 MHz, CDCl3 8.60(1H, d, J=1.5Hz), 8.05(1H, dd,J=1.6Hz, 8.7Hz), 7.70(1H, d, J=8.7Hz), 7.62(2H, d, J=8.2Hz), 7.49(2H, d,J=8.2Hz), 7.31(2H, d, J=8.8Hz), 7.27-7.23(2H, m), # 7.06(2H, t,J=8.6Hz), 6.80(2H, d, J=8.8Hz), 5.05(2H, s), 4.38 (1H, m), 3.06(6H, s),2.45-2.20(2H, m), 2.10-1.70(5H, m), 1.50-1.20(3H, m)

[2215] TABLE 258 Ex- am- ple >90% No. Purity (NMR) 1H NMR(δ) ppm 440

MS 557 (M + 1) 300 MHz, DMSO-d6 8.20 (1H, s), 7.86 (2H, m), 7.39 ( 1H,d, J = 7.9 Hz), 7.34 (1H, d, J = 7 .9 Hz), 7.07 (2H, dt, J = 2.3 Hz, 8.6 Hz), 6.98-6.88 (5H, m), 6.83 (1 H, d, J = 8.3 Hz), 5.91 (1H, s), 3.96(1H, m), 2.30-1.95 (2H, m), 1.9 0-1.50 (4H, m), 1.40-1.10 (3H, m ) 441

MS 557 (M + 1) 300 MHz, DMSO-d6 8.24 (1H, d, J = 1.4 Hz), 8.01 (1H, d, J= 8.8 Hz), 7.91 (1H, dd, J = 1.4 Hz, 8.7 Hz), 7.47 (1H, t, J = 8.4 Hz ),7.43-7.35 (2H, m), 7.15-7.01 (5H, m), 6.92 (2H, d, J = 10.4 Hz), 6.11(1H, s), 3.90 (1H, m), 2.30-1.95 (2H, m), 1.90-1.50 (4H, m), 1.40-1.10(3H, m) 442

MS 610 (M + 1) 300 Mz, DMSO-d6 8.26 (1H, d, J = 1.5 Hz), 8.11 (1H, d, J= 8.9 Hz), 7.96 (1H, dd, J = 8.9 , 1.5 Hz), 7.65-7.57 (5H, m), 7.4 7(1H, t, J = 7.7 Hz), 7.35 (1H, d, J =7.6 Hz), 7.30-7.22 (3H, m), 7.1 6(1H, dd, J = 8.7, 2.3 Hz), 6.88 # (1 H, s), 4.04 (1H, brt, J = 11.3 Hz),2.98 (3H, s) 2.84 (3H, s), 2.30-2 .10 (2H, brm), 1.94-1.75 (4H, br m),1.68-1.57 (1H, brm), 1.45-1 .14 (3H, brm)

[2216] TABLE 259 Ex- am- ple No. 443

444

445

Example No. Purity >90% (NMR) 1H NMR (δ) ppm 443 MS 666 (M + 1) 300 Mz,DMSO-d6 8.23 (1H, s), 7.98and7.89 (2H, A Bq, J = 8.8 Hz), 7.62-7.06(11H, m ), 6.86 (1H, s), 4.12-3.77 (2H, b rm), 3.72 (1H, brs), 3.69 (1H,br s), 3.18 (1H, brs), 3.05 (1H, brs ), 2.31-2.08 (2H, brm), 1.90-1. 54(7H, brm), 1.48-1.13 (5H, brm ) 444 MS 718 (M + 1) 300 MHz, DMSO-d6 8.36(1H, s), 8.00 (1H, d, J = 8.7 H z), 7.90 (1H, d, J = 9.3 Hz), 7.80- 7.70(2H, m), 7.63 (2H, d, J = 8.4 H z), 7.32 (2H, t, J = 8.7 Hz), 7.22 ( 2H,d, J = 8.4 Hz), 5.62 (1H, d, J = 7 .5 Hz), 5.57 (1H, brd, J = 4.8 Hz),5.41 (2H, s), 5.31 (1H, m), 4.29 ( 1H, m), 3.84 (1H, d, J = 9.0 Hz), 3.50-3.20 (3H, m), 2.71 (3H, s), 2. 40-2.20 (2H, m), 1.75-1.60 (1H, m),1.50-1.20 (3H, m) 445 MS 733 (M + 1) 300 MHz, DMSO-d6 8.36 (1H, s), 8.00(1H, d, J = 8.7 H z), 7.92 (1H, d, J = 9.3 Hz), 7.57 ( 1H, t, J = 8.4Hz), 7.50-7.35 (6H, m), 7.25-7.05 (4H, m), 6.82 (1H, s), 5.62 (1H, d, J= 7.2 Hz), 5.56 ( 1H, m), 5.28 (1H, brs), 3.95 (1H, m), 3.82 (1H, d, J =8.7 Hz), 3.50- 3.20 (3H, m), 2.30-2.05 (2H, m), 1.90-1.55 (5H, m),1.40-1.10 (3 H, m)

[2217] TABLE 260 Ex- am- ple >90% No. Purity (NMR) 1H NMR (δ) ppm 446

MS 674 (M + 1) 300 MHz, DMSO-d6 8.29 (1H, s), 8.13 (1H, d, J = 9.0 H z),7.97 (1H, d, J = 9.0 Hz), 7.63 ( 1H, t, J = 8.6 Hz), 7.51-7.32 (7H, m),7.15 (1H, d, J = 12.0 Hz), 7.03 (1H, d, J = 9.0 Hz), 5.10 (2H, s), # 4.09 (1H, m), 3.82 (2H, t, J = 6.3 Hz ), 3.56 (2H, t, J = 7.4 Hz), 2.45(2 H, m), 2.40-2.10 (2H, m), 2.00-1 .55 (5H, m), 1.50-1.20 (3H, m) 702

MS 641 (M + 1) 300 MHz, DMSO-d6 8.97 (1H, d, J = 1.8 Hz), 8.52 (1H, d, J= 2.4 Hz), 8.36 (1H, d, J = 7.8 H z), 8.16 (1H, s), 7.96 (!H, d, J = 8.1 Hz), 7.55-7.40 (5H, m), 7.14 (1H, d, J = 12.6 Hz), 7.01 (1H, dd, J=8.4 Hz, 1.8 Hz), 5.11 (2H, s), 4. # 20-3.95 (2H, m), 2.65-2.45 (2H, m),1.95-1.80 (5H, m), 1.20-1.1 0 (3H, m) 703

MS 653 (M + 1) 300 MHz, DMSO-d6 8.97 (1H, d, J = 1.8 Hz), 8.52 (1H, d, J= 1.8 Hz), 7.82 (1H, s), 7.70-7.35 (7H, m), 7.13 (1H, d, J = 12.3 Hz),7.00 (1H, d, J = 11.1 Hz), 5.1 4 (2H, s), 3.60-3.35 (4H, m), 2.6 5-2.40(2H, m), 2.00-2.55 (9H, m ), 1.40-1.10 (3H, m)

[2218] Formulation Example is given in the following. This example ismerely for the purpose of exemplification and does not limit theinvention. (a) compound of Example 1 10 g (b) lactose 50 g (c) cornstarch 15 g (d) sodium carboxymethylcellulose 44 g (e) magnesiumstearate 1 g

[2219] The entire amounts of (a), (b) and (c) and 30 g of (d) arekneaded with water, dried in vacuo and granulated. The obtained granulesare mixed with 14 g of (d) and 1 g of (e) and processed into tabletswith a tableting machine to give 1000 tablets each containing 10 mg of(a).

INDUSTRIAL APPLICABILITY

[2220] As is evident from the above-mentioned results, the compound ofthe present invention shows a high inhibitory activity against HCVpolymerase.

[2221] Therefore, the compound of the present invention can provide apharmaceutical agent effective for the prophylaxis or treatment ofhepatitis C, based on the anti-HCV effect: afforded by the HCVpolymerase inhibitory activity. When used concurrently with a differentanti-HCV agent, such as interferon, and/or an anti-inflammatory agentand the like, it can provide a pharmaceutical agent more effective forthe prophylaxes or treatment of hepatitis C. Its high inhibitoryactivity specific to HCV polymerase suggests the possibility of thecompound being a pharmaceutical agent with slight side effects, whichcan be used safely for humans.

[2222] This application is based on patent application Nos. 369008/1999,391904/2000 and 193786/2001 filed in Japan, and internationalapplication No. PCT/JP00/09181, the contents of which are herebyincorporated by reference.

What is claimed is:
 1. A therapeutic agent for hepatitis C, whichcomprises a fused ring compound of the following formula [I] or apharmaceutically acceptable salt thereof as an active ingredient:

wherein a broken line is a single bond or a double bond, G¹ is C(—R¹) ora nitrogen atom, G² is C(—R²) or a nitrogen atom, G³ is C(—R³) or anitrogen atom, G⁴ is C (—R⁴) or a nitrogen atom, G⁵, G⁶, G⁸ and G⁹ areeach independently a carbon atom or a nitrogen atom, G⁷ is C(—R⁷), anoxygen atom, a sulfur atom, or a nitrogen atom optionally substituted byR⁸, wherein R¹, R², R³ and R⁴ are each independently, (1) hydrogen atom,(2) C₁₋₆ alkanoyl, (3) carboxyl, (4) cyano, (5) nitro, (6) C₁₋₆ alkyloptionally substituted by 1 to 3 substituent(s) selected from thefollowing group A, group A; halogen atom, hydroxyl group, carboxyl,amino, C₁₋₆ alkoxy, C₁₋₆ alkoxy C₁₋₆ alkoxy, C₁₋₆ alkoxycarbonyl andC₁₋₆ alkylamino, (7) —COOR^(a1) wherein R^(a1) is optionally substitutedC₁₋₆ alkyl (as defined above), C₆₋₁₄ aryl C₁₋₆ alkyl optionallysubstituted by 1 to 5 substituent(s) selected from the following group Bor glucuronic acid residue, group B; halogen atom, cyano, nitro, C₁₋₆alkyl, halogenated C₁₋₆ alkyl, C₁₋₆ alkanoyl, —(CH₂)_(r)—COOR^(b1),—(CH₂)_(r)—CONR^(b1)R^(b2), —(CH₂)_(r)—NR^(b1)R^(b2),—(CH₂)_(r)—NR^(b1)—COR^(b2), —(CH₂)_(r)—NHSO₂R^(b1), —(CH₂)_(r)—OR^(b1),—(CH₂)_(r)—SR^(b1), —(CH₂)_(r)—SO₂R^(b1) and —(CH₂)_(r)—SO₂NR^(b1)R^(b2)wherein R^(b1) and R^(b2) are each independently hydrogen atom or C₁₋₆alkyl and r is 0 or an integer of 1 to 6, (8) —CONR^(a2)R^(a3) whereinR^(a2) and R^(a3) are each independently hydrogen atom, C₁₋₆ alkoxy oroptionally substituted C₁₋₆ alkyl (as defined above), (9) —C(═NR^(a4))NH₂ wherein R^(a4) is hydrogen atom or hydroxyl group, (10) —NHR^(a5)wherein R^(a5) is hydrogen atom, C₁₋₆ alkanoyl or C₁₋₆ alkylsulfonyl,(11) —OR^(a6) wherein R^(a6) is hydrogen atom or optionally substitutedC₁₋₆ alkyl(as defined above), (12) —SO₂R^(a7) wherein R^(a7) is hydroxylgroup, amino, C₁₋₆ alkyl or C₁₋₆ alkylamino, (13) —P(═O) (OR^(a31))₂wherein R^(a31) is hydrogen atom, optionally substituted C₁₋₆ alkyl (asdefined above) or C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B or (14) heterocyclicgroup having 1 to 4 heteroatom(s) selected from an oxygen atom, anitrogen atom and a sulfur atom, and R⁷ and R⁸ are each hydrogen atom oroptionally substituted C₁₋₆ alkyl (as defined above), ring Cy is (1)C₃₋₈ cycloalkyl optionally substituted by 1 to 5 substituent(s) selectedfrom the following group C, group C; hydroxyl group, halogen atom, C₁₋₆alkyl and C₁₋₆ alkoxy, (2) C₃₋₈ cycloalkenyl optionally substituted by 1to 5 substituent(s) selected from the above group: C, or

wherein u and v are each independently an integer of 1 to 3, ring A is(1) C₆₋₁₄ aryl, (2) C₃₋₈ cycloalkyl, (3) C₃₋₈ cycloalkenyl or (4)heterocyclic group having 1 to 4 heteroatom(s) selected from an oxygenatom, a nitrogen atom and a sulfur atom, R⁵ and R⁶ are eachindependently (1) hydrogen atom, (2) halogen atom, (3) optionallysubstituted C₁₋₆ alkyl (as defined above) or (4) —OR^(a8) wherein R^(a8)is hydrogen atom, C₁₋₆ alkyl or C₆₋₁₄ aryl C₁₋₆ alkyl, and X is (1)hydrogen atom, (2) halogen atom, (3) cyano, (4) nitro, (5) amino, C₁₋₆alkanoylamino, (6) C₁₋₆ alkylsulfonyl, (7) optionally substituted C₁₋₆alkyl (as defined above), (8) C₂₋₆ alkenyl optionally substituted by 1to :3 substituent(s) selected from the above group A, (9) —COOR^(a9)wherein R^(a9) is hydrogen atom or C₁₋₆ alkyl, (10)—CONH—(CH₂)_(l)—R^(a10) wherein R^(a10) is optionally substituted C₁₋₆alkyl (as defined above), C₁₋₆ alkoxycarbonyl or C₁₋₆ alkanoylamino and1 is 0 or an integer of 1 to 6, (11) —OR^(a11) wherein R^(a11) ishydrogen atom or optionally substituted C₁₋₆ alkyl (as defined above) or

wherein ring B is (1′) C₆₋₁₄ aryl, (2′) C₃₋₈ cycloalkyl or (3′)heterocyclic group (as defined above), each Z is independently (1′) agroup selected from the following group D, (2′) C₆₋₁₄ aryl optionallysubstituted by 1 to 5 substituent(s) selected from the following groupD, (3′) C₃₋₈ cycloalkyl optionally substituted by 1 to 5 substituent(s)selected from the following group D, (4′) C₆₋₁₄ aryl C₁₋₆ alkyloptionally substituted by 1 to 5 substituent(s) selected from tilefollowing group D, (5′) heterocyclic group optionally substituted by 1to 5 substituent(s) selected from the following group D,  wherein theheterocyclic group has 1 to 4 heteroatom(s) selected from an oxygenatom, a nitrogen atom and a sulfur atom, or (6′) heterocycle C₁₋₆ alkyloptionally substituted by 1 to 5 substituent(s) selected from thefollowing group D,  wherein the heterocycle C₁₋₆ alkyl is C₁₋₆ alkylsubstituted by heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the group D, as defined above, group D: (a)hydrogen atom, (b) halogen atom, (c) cyano, (d) nitro, (e) optionallysubstituted C₁₋₆ alkyl (as defined above), (f) —(CH₂)_(t)—COR^(a18),(hereinafter each t means independently 0 or an integer of 1 to 6),wherein R^(a18) is (1″) optionally substituted C₁₋₆ alkyl (as definedabove), (2″) C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the above group B or (3″) heterocyclic group optionallysubstituted by 1 to 5 substituent(s) selected from the above group B wherein the heterocyclic group has 1 to 4 heteroatom(s) selected froman oxygen atom, a nitrogen atom and a sulfur atom, (g)—(CH₂)_(t)—COOR^(a19) wherein R^(a19) is hydrogen atom, optionallysubstituted C₁₋₆ alkyl (as defined above) or C₆₋₁₄ aryl C₁₋₆ alkyloptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B, (h) —(CH₂)_(t)—CONR^(a27)R^(a28) wherein R^(a27) and R^(a28)are each independently, (1″) hydrogen atom, (2″) optionally substitutedC₁₋₆ alkyl (as defined above), (3″) C₆₋₁₄ aryl optionally substituted by1 to 5 substituent(s) selected from the above group B, (4″) C₆₋₁₄ arylC₁₋₆ alkyl optionally substituted by 1 to 5 substituent(s) selected fromthe above group B, (5″) heterocyclic group optionally substituted by 1to 5 substituent(s) selected from the above group B, (6″) heterocycleC₁₋₆ alkyl optionally substituted by 1 to 5 substituent(s) selected fromthe above group B,  wherein the heterocycle C₁₋₆ alkyl is C₁₋₆ alkylsubstituted by heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B, as defined above, (7″)C₃₋₈ cycloalkyl optionally substituted by 1 to 5 substituent(s) selectedfrom the above group B, (8″) C₃₋₈ cycloalkyl C₁₋₆ alkyl optionallysubstituted by 1 to 5 substituent s) selected from the above group B,(9″) hydroxyl group or (10″) C₁₋₆ alkoxy, (i) —(CH₂)_(t)—C(═NR^(a33))NH₂wherein R^(a33) is hydrogen atom, C₁₋₆ alkyl, hydroxyl group or C₁₋₆alkoxy, (j) —(CH₂)_(t)—OR^(a20) wherein R^(a20) is (1″) hydrogen atom,(2″) optionally substituted C₁₋₆ alkyl (as defined above), (3″)optionally substituted C₂₋₆ alkenyl (as defined above), (4″) C₂₋₆alkynyl optionally substituted by 1 to 3 substituent(s) selected fromthe above group A, (5″) C₆₋₁₄ aryl optionally substituted by 1 to 5substituent(s) selected from the above group B, (6″) C₆₋₁₄ aryl C₁₋₆alkyl optionally substituted by 1 to 5 substituent(s) selected from theabove group B, (7″) heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B, (8″) heterocycle C₁₋₆alkyl optionally substituted by 1 to 5 substituent(s) selected from theabove group B, (9″) C₃₋₈ cycloalkyl optionally substituted by 1 to 5substituent(s) selected from the above group B, or (10″) C₃₋₈ cycloalkylC₁₋₆ alkyl optionally substituted by 1 to 5 substituent(s) selected fromthe above group) B, (k) —(CH₂)_(t)—O—(CH₂)_(p)—COR^(a21) wherein R^(a21)is amino, C₁₋₆ alkylamino or heterocyclic group optionally substitutedby 1 to 5 substituent(s) selected from the above group B, and p is 0 oran integer of 1 to 6, (l) —(CH₂)_(t)—NR^(a22)R^(a23) wherein R^(a22) andR^(a23) are each independently (1″) hydrogen atom, (2″) optionallysubstituted C₁₋₆ alkyl (as defined above), (3″) C₆₋₁₄ aryl optionallysubstituted by 1 to 5 substituent(s) selected from the above group B, (4″) C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5 substituent(s)selected from the above group B, (5″) heterocycle C₁₋₆ alkyl optionallysubstituted by 1 to 5 substituent(s) selected from the above group B or(6″) heterocyclic group optionally substituted by 1 to 5 substituent(s)selected from the above group B, (m) —(CH₂)_(t)—NR^(a29)CO—R^(a24)wherein R^(a29) is hydrogen atom, C₁₋₆ alkyl or C₁₋₆ alkanoyl, andR^(a24) is (1″) amino, (2″) C₁₋₆ alkylamino, (3″) optionally substitutedC₁₋₆ alkyl (as defined above), (4″) C₆₋₁₄ aryl optionally substituted by1 to 5 substituent(s) selected from the(above group B, (5″) heterocyclicgroup optionally substituted by 1 to 5 substituent(s) selected from theabove group B or (6″) heterocycle C₁₋₆ alkyl optionally substituted by 1to 5 substituent(s) selected from the above group B, (n)—(CH₂)_(t)—NR^(a29) SO₂—R^(a25) wherein R^(a29) is as defined above, endR^(a25) is hydrogen atom, optionally substituted C₁₋₆ alkyl (as definedabove), C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the above group B or heterocyclic group optionallysubstituted by 1 to 5 substituent(s) selected from the above group B,(o) —(CH₂)_(t)—S (O)_(q)—R^(a25) wherein R^(a25) is as defined above,and q is 0, 1 or 2, (p) —(CH₂)_(t)—SO₂—NHR^(a26) wherein R^(a26) ishydrogen atom, optionally substituted C₁₋₆ alkyl (as defined above),C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s) selected fromthe above group B or heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B, and (q) heterocyclicgroup having 1 to 4 heteroatom(s) selected from an oxygen atom, anitrogen atom and a sulfur atom, and w is an integer of 1 to 3, and Y is(1′) a single bond, (2′) C₁₋₆ alkylene, (3′) C₂₋₆ alkenylene, (4′)—(CH₂)_(m)—O—(CH₂)_(n)—, (hereinafter m and n are each independently 0or an integer of 1 to 6), (5′) —CO—, (6′ ) —CO₂—(CH₂)_(n)—, (7′ )—CONH—(CH₂)_(n)—NH—, (8′) —NHCO₂—, (9′) —NHCONH—, (10′)—O—(CH₂)_(n)—CO—, (11′) —O—(CH₂)_(n)—O—, (12′) —SO₂—, (13′)—(CH₂)_(m)—NR^(a12)—(CH₂)_(n)— wherein R^(a12) is (1″) hydrogen atom,(2″) optionally substituted C₁₋₆ alkyl (as defined above), (3′) C₆₋₁₄aryl C₁₋₆ alkyl optionally substituted by 1 to 5 substituent(s) selectedfrom the above group B, (4″) C₆₋₁₄ aryl optionally substituted by 1 to 5substituent(s) selected from the above group B, (5″) —COR^(b5)  whereinR^(b5) is hydrogen atom, optionally substituted C₁₋₆ alkyl (as definedabove), C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the above group B or C₆₋₁₄ aryl C₁₋₆ alkyl optionallysubstituted by 1 to 5 substituent(s) selected from the above group B,(6″) —COOR^(b5) (R^(b5) is as defined above) or (7″) —SO₂R^(b5) (R^(b5)is as defined above), (14′) —NR^(a12)CO— (R^(a12) is as defined above),(15′) —CONR^(a13)—(CH₂)_(n)— wherein R^(a13) is hydrogen atom,optionally substituted C₁₋₆ alkyl (as defined above) or C₆₋₁₄ aryl C₁₋₆alkyl optionally substituted by 1 to 5 substituent(s) selected from theabove group B, (16′) —CONH—CHR^(a14)— wherein R^(a14) is C₆₋₁₄ aryloptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B, (17′) —O—(CH₂)_(m)CR^(a15)R^(a16)—(CH₂)_(n)— wherein R^(a15)and R^(a16) are each independently (1″) hydrogen atom, (2″) carboxyl,(3″) C₁₋₆ alkyl, (4″) —OR^(b6) wherein R^(b6) is C₁₋₆ alkyl or C₆₋₁₄aryl C₁₋₆ alkyl, or (5″) —NHR^(b7) wherein R^(b7) is hydrogen atom, C₁₋₆alkyl, C₁₋₆ alkanoyl or C₆₋₁₄ aryl C₁₋₆ alkyloxycarbonyl, or R^(a15) isoptionally

wherein n′, ring B′, Z′ and w′ are the same as the above-mentioned n,ring B, Z and w, respectively, and may be the same as or different fromthe respective counterparts, (18′)—(CH₂)_(n)—NR^(a12)—CHR^(a15)—(R^(a12) and R^(a15) are each as definedabove), (19′) —NR^(a17)SO₂— wherein R^(a17) is hydrogen atom or C₁₋₆alkyl, (20′) —S(O)_(e)—(CH₂)_(m)CR^(a15)R^(a16)—(CH₂)_(n)—(e is 0, 1 or2, R^(a15) and R^(a16) are each as defined above), or (21′)—(CH₂)_(m)—CR^(a15)R^(a16)—(CH₂)_(n)—(R^(a15) and R^(a16) are each asdefined above).
 2. The therapeutic agent of claim 1, wherein 1 to 4 ofthe G¹, G², G³, G⁴, G⁵, G⁶, G⁷, G⁸ and G⁹ is(are) a nitrogen atom. 3.The therapeutic agent of claim 2, wherein G² is C(—R²) and G⁶ is acarbon atom.
 4. The therapeutic agent of claim 2, wherein G⁵ is anitrogen atom.
 5. The therapeutic agent of claim 1, wherein, in formula[I], the moiety

is a fused ring selected from


6. The therapeutic agent of claim 5, wherein, in formula [I], the moiety

is a fused ring selected from


7. The therapeutic agent of claim 6, which comprises a fused ringcompound of the following formula [I-1]

wherein each symbol is as defined in claim 1, or a pharmaceuticallyacceptable salt thereof as an active ingredient.
 8. The therapeuticagent of claim 6, which comprises a fused ring compound of the followingformula [I-2]

wherein each symbol is as defined in claim 1, or a pharmaceuticallyacceptable salt thereof as an active ingredient.
 9. The therapeuticagent of claim 6, which comprises a fused ring compound of the followingformula [I-3]

wherein each symbol is as defined in claim 1, or a pharmaceuticallyacceptable salt thereof as an active ingredient.
 10. The therapeuticagent of claim 6, which comprises a fused ring compound of the followingformula [I-4]

wherein each symbol is as defined in claim 1, or a pharmaceuticallyacceptable salt thereof as an active ingredient.
 11. The therapeuticagent of claim 1, wherein at least one of R¹, R², R³ and R⁴ is carboxyl,—COOR^(a1), —CONR^(a2)R^(a3), —SO₂R^(a7) (wherein R^(a1), R^(a2), R^(a3)and R^(a7) are as defined in claim 1),


12. The therapeutic agent of claim 11, wherein at least one of R¹, R²,R³ and R⁴ is carboxyl, —COOR^(a1), —CONR^(a2)R^(a3) or —SO₂R^(a7)wherein R^(a1), R^(a2), R^(a3) and R^(a7) are as defined in claim
 1. 13.The therapeutic agent of claim 1, wherein at least one of R¹, R², R³ andR⁴ is —COOR^(a1) wherein R^(a1) is glucuronic acid residue.
 14. Thetherapeutic agent of claim 1, wherein at least one of R¹, R², R³ and R⁴is heterocyclic group having 1 to 4 heteroatom(s) selected from anoxygen atom, a nitrogen atom and a sulfur atom.
 15. The therapeuticagent of claim 1, wherein the ring Cy is cyclopentyl, cyclohexyl,cycloheptyl, tetrahydrothiopyranyl or piperidino.
 16. The therapeuticagent of claim 1, wherein the ring Cy is

wherein each symbol is as defined in claim
 1. 17. The therapeutic agentof claim 1, wherein the ring A is C₆₋₁₄ aryl.
 18. The therapeutic agentof claim 1, wherein at least one substituent optionally substituted bygroup A is a substituent substituted by C₁₋₆ alkoxy C₁₋₆ alkoxy.
 19. Thetherapeutic agent of claim 1, wherein the Y is;—(CH₂)_(m)—CR^(a15)R^(a16)—(CH₂)_(n)— wherein each symbol is as definedin claim
 1. 20. The therapeutic agent of claim 1, wherein at least onegroup represented by Z is heterocycle C₁₋₆ alkyl optionally substitutedby 1 to 5 substituent(s) selected from the group D.
 21. The therapeuticagent of claim 1, wherein at least one group represented by Z is aheterocyclic group optionally substituted by 1 to 5 substituent(s)selected from the group D, wherein said heterocyclic group is selectedfrom the following groups:

wherein E¹ is an oxygen atom, a sulfur atom or N(—R^(a35)) E² is anoxygen atom, CH₂ or N(—R^(a35)), E³ is an oxygen atom or a sulfur atom,wherein each R^(a35) is independently hydrogen atom or C₁₋₆ alkyl, f isan integer of 1 to 3, and h and h′ are the same or different and each isan integer of 1 to
 3. 22. The therapeutic agent of claim 21, wherein atleast one group represented by Z is heterocyclic group optionallysubstituted by 1 to 5 substituent(s) selected from the group D whereinsaid heterocyclic group is selected from the following groups:

wherein each symbol is as defined in claim
 21. 23. The therapeutic agentof claim 1, wherein at least one group represented by group D is—(CH₂)_(t)—CONR^(a27)R^(a28) wherein each symbol is as defined in claim1, and at least one of R^(a27) and R^(a28) is C₁₋₆ alkoxy.
 24. Thetherapeutic agent of claim 1, wherein at least one group represented bygroup D is —(CH₂)_(t)—C(═NR^(a33) )NH₂ wherein each symbol is as definedin claim 1, and R^(a33) is hydroxyl group oI° C₁₋₆ alkoxy.
 25. Thetherapeutic agent of claim 1, wherein at least one group represented bygroup D is —(CH₂)_(t)—O—(CH₂)_(p)—COR^(a21), wherein each symbol is asdefined in claim 1, and R^(a21) is amino.
 26. The therapeutic agent ofclaim 1, wherein at least one group represented by group D is—(CH₂)_(t)—NR^(a29)CO—R^(a24) wherein each symbol is as defined in claim1, and R^(a24) is amino or C₁₋₆ alkylamino.
 27. The therapeutic agent ofclaim 1, wherein at least one group represented by group D is—(CH₂)_(t)—NR^(a22)R^(a23) wherein each symbol is as defined in claim 1,and at lease one of R^(a22) and R^(a23) is heterocyclic group optionallysubstituted by 1 to 5 substituent(s) selected from the group B.
 28. Thetherapeutic agent of claim 1, wherein at least one group represented bygroup D is heterocyclic group having 1 to 4 heteroatom(s) selected froman oxygen atom, a nitrogen atom and a sulfur atom.
 29. The therapeuticagent of claim 1, which comprises a fused ring compound of the followingformula [I] or a pharmaceutically acceptable salt thereof as an activeingredient:

wherein a broken line is a single bond or a double bond, G¹ is C(—R¹) ora nitrogen atom, G² is C(—R²) or a nitrogen atom, G³ is C(—R³) or anitrogen atom, G⁴ is C(—R⁴) or a nitrogen atom, G⁵, G⁶, G⁸ and G⁹ areeach independently a carbon atom or a nitrogen atom, G⁷ is C(—R⁷), anoxygen atom, a sulfur atom, or a nitrogen atom optionally substituted byR⁸, wherein R¹, R², R³ and R⁴ are each independently, (1) hydrogen atom,(2) C₁₋₆ alkanoyl, (3) carboxyl, (4) cyano, (5) nitro, (6) C₁₋₆ alkyloptionally substituted by 1 to 3 substituent(s) selected from thefollowing group A, group A; halogen atom, hydroxyl group, carboxyl,amino, C₁₋₆ alkoxy, C₁₋₆ alkoxycarbonyl and C₁₋₆ alkylamino, (7)—COOR^(a1) wherein R^(a1) is optionally substituted C₁₋₆ alkyl (asdefined above) or C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the following group B, group B; halogenatom, cyano, nitro, C₁₋₆ alkyl, halogenated C₁₋₆ alkyl, C₁₋₆ alkanoyl,—(CH₂)_(r)—COOR^(b1), —(CH₂)_(r)—CONR^(b1)R^(b2),—(CH₂)_(r)—NR^(b1)R^(b2), —(CH₂)_(r)—NR^(b1)—COR^(b2),—(CH₂)_(r)—NHSO₂R^(b1), —(CH₂)_(r)—OR^(b1), —(CH₂)_(r)—SR^(b1),—(CH₂)_(r)—SO₂R^(b1) and —(CH₂)_(r)—SO₂NR^(b1)R^(b2) wherein R^(b1) andR^(b2) are each independently hydrogen atom or C₁₋₆ alkyl and r is 0 oran integer of 1 to 6, (8) —CONR^(a2)R^(a3) wherein R^(a2) and R^(a3) areeach independently hydrogen atom, C₁₋₆ alkoxy or optionally substitutedC₁₋₆ alkyl (as defined above), (9) —C(═NR^(a4))NH₂ wherein R^(a4) ishydrogen atom or hydroxyl group, (10) —NHR^(a5) wherein R^(a5) ishydrogen atom, C₁₋₆ alkanoyl or C₁₋₆ alkylsulfonyl, (11) —OR^(a6)wherein R^(a6) is hydrogen atom or optionally substituted C₁₋₆ alkyl (asdefined above), (12) —SO₂R^(a7) wherein R^(a7) is hydroxyl group, amino,C₁₋₆ alkyl or C₁₋₆ alkylamino or (13) —P(═O) (OR^(a31))₂ wherein R^(a31)is hydrogen atom, optionally substituted C₁₋₆ alkyl (as defined above)or C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5 substituent(s)selected from the above group B, and R⁷ and R⁸ are each hydrogen atom oroptionally substituted C₁₋₆ alkyl (as defined above), ring Cy is (1)C₃₋₈ cycloalkyl optionally substituted by 1 to 5 substituent(s) selectedfrom the following group C, group C; hydroxyl group, halogen atom, C₁₋₆alkyl and C₁₋₆ alkoxy, (2) C₃₋₈ cycloalkenyl optionally substituted by 1to 5 substituent(s) selected from the above group C, or

wherein u and v are each independently an integer of 1 to 3, ring A is(1) C₆₋₁₄ aryl, (2) C₃₋₈ cycloalkyl, (3) C₃₋₈ cycloalkenyl or (4)heterocyclic group having 1 to 4 heteroatom(s) selected from an oxygenatom, a nitrogen atom and a sulfur atom, R⁵ and R⁶ are eachindependently (1) hydrogen atom, (2) halogen atom, (3) optionallysubstituted C₁₋₆ alkyl (as defined above) or (4) —OR^(a8) wherein R^(a8)is hydrogen atom, C₁₋₆ alkyl or C₁₋₁₄ aryl C₁₋₆ alkyl, and X is (1)hydrogen atom, (2) halogen atom, (3) cyano, (4) nitro, (5) amino, C₁₋₆alkanoylamino, (6) C₁₋₆ alkylsulfonyl, (7) optionally substituted C₁₋₆alkyl (as defined above), (8) C₂₋₆ alkenyl optionally substituted by 1to 3 substituent(s) selected from the above group A, (9) —COOR^(a9)wherein R^(a9) is hydrogen atom or C₁₋₆ alkyl, (10)—CONH—(CH₂)_(l)—R^(a10) wherein R^(a10) is optionally substituted C₁₋₆alkyl (as defined above), C₁₋₆ alkoxycarbonyl or C₁₋₆ alkanoylamino and1 is 0 or an integer of 1 to 6, (11) —OR^(a11) wherein R^(a11) ishydrogen atom or optionally substituted C₁₋₆ alkyl (as defined above) or

wherein ring B is (1′) C₆₋₁₄ aryl, (2′) C₃₋₈ cycloalkyl or (3′)heterocyclic group (as defined above), each Z is independently (1′) agroup selected from the following group D, (2′) C₆₋₁₄ aryl optionallysubstituted by 1 to 5 substituent(s) selected from the following groupD, (3′) C₃₋₈ cycloalkyl optionally substituted by 1 to 5 substituent(s)selected from the following group D, (4′) C₆₋₁₄ aryl C₁₋₆ alkyloptionally substituted by 1 to 5 substituent(s) selected from thefollowing group D or (5′) heterocyclic group optionally substituted by 1to 5 substituent(s) selected from the following group D  wherein theheterocyclic group has 1 to Z: heteroatom(s) selected from an oxygenatom, a nitrogen atom and a sulfur atom,  group D: (a) hydrogen atom,(b) halogen atom, (c) cyano, (d) nitro, (e) optionally substituted Cl-6alkyl (as defined above), (f) —(CH₂)_(t)—COR^(a18), (hereinafter each tmeans independently 0 or an integer of 1 to 6), wherein R^(a18) is (1″)optionally substituted C₁₋₆ alkyl (as defined above), (2″) C₆₋₁₄ aryloptionally substituted by 1 to 5 substituent(s) selected front the abovegroup B or (3″) heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B  wherein the heterocyclicgroup has 1 to 4 heteroatom(s) selected front an oxygen atom, a nitrogenatom and a sulfur atom, (g) —(CH₂)_(t)—COOR^(a19) wherein R^(a19) ishydrogen atom, optionally substituted C₁₋₆ alkyl (as defined above) orC₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5 substituent(s)selected from the above group B, (h) —(CH₂)_(t)—CONR^(a27)R^(a28)wherein R^(a27) and R^(a28) are each independently, (1″) hydrogen atom,(2″) optionally substituted C₁₋₆ alkyl (as defined above), (3″) C₆₋₁₄aryl optionally substituted by 1 to 5 substituent(s) selected from theabove group (4″) C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B, (5″) heterocyclic groupoptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B, (6″) heterocycle C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B,  wherein the heterocycleC₁₋₆ alkyl is C₁₋₆ alkyl substituted by heterocyclic group optionallysubstituted by 1 to 5 substituent(s) selected from the above group B, asdefined above, (7″) C₃₋₈ cycloalkyl optionally substituted by 1 to 5substituent(s) selected from the above group B, or (8″) C₃₋₈ cycloalkylC₁₋₆ alkyl optionally substituted by 1 to 5 substituent(s) selected fromthe above group B, (i) —(CH₂)_(t)—C(═NR^(a33))NH₂ wherein R^(a33) ishydrogen atom or C₁₋₆ alkyl, (j) —(CH₂)_(t)—OR^(a20) wherein R^(a20) is(1″) hydrogen atom, (2″) optionally substituted C₁₋₆ alkyl (as definedabove), (3″) optionally substituted C₂₋₆ alkenyl (as defined above),(4″) C₂₋₆ alkynyl optionally substituted by 1 to 3 substituent(s)selected from the above group A, (5″) C₆₋₁₄ aryl optionally substitutedby 1 to 5 substituent(s) selected from the above group B, (6″) C₆₋₁₄aryl C₁₋₆ alkyl optionally substituted by 1 to 5 substituent(s) selectedfrom the above group B, (7″) heterocyclic group optionally substitutedby 1 to 5 substituent(s) selected from the above group B, (8″)heterocycle C₁₋₆ alkyl optionally substituted by 1 to 5 substituent(s)selected from the above group B, (9″) C₃₋₈ cycloalkyl optionallysubstituted by 1 to 5 substituent(s) selected from the above group B, or(10″) C₃₋₈ cycloalkyl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B, (k)—(CH₂)_(t)—O—(CH₂)_(p)—COR^(a21) wherein R^(a21) is C₁₋₆ alkylamino orheterocyclic group optionally substituted by 1 to 5 substituent(s)selected from the above group B, and p is 0 or an integer of 1 to 6, (1)—(CH₂)_(t)—NR^(a22)R^(a23) wherein R^(a22) and R^(a23) are eachindependently (1″) hydrogen atom, (2″) optionally substituted C₁₋₆ alkyl(as defined above), (3″) C₆₋₁₄ aryl optionally substituted by 1 to 5substituent(s) selected from the above group B, (4″) C₆₋₁₄ aryl C₁₋₆alkyl optionally substituted by 1 to 5 substituent(s) selected from theabove group) B or (5″) heterocycle C₁₋₆ alkyl optionally substituted by1 to 5 substituent(s) selected from the above group B, (m)—(CH₂)_(t)—NR^(a29)CO—R^(a24) wherein R^(a29) is hydrogen atom, C₁₋₆alkyl or C₁₋₆ alkanoyl, R^(a24) is optionally substituted C₁₋₆ alkyl (asdefined above), C₆₋₁₄ aryl optionally substituted by 1 to 5substituent(s) selected from the above group B or heterocyclic groupoptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B, (n) —(CH₂)_(t)—NHSO₂—R^(a25) wherein R^(a25) is hydrogen atom,optionally substituted C₁₋₆ alkyl (as defined above), C₆₋₁₄ aryloptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B or heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B, (o)(CH₂)_(t)—S(O)_(q)—R^(a25) wherein R^(a25) is as defined above, and q is0, 1 or 2, and (p) —(CH₂)_(t)—SO₂—NHR^(a26) wherein R^(a26) is hydrogenatom, optionally substituted C₁₋₆ alkyl (as defined above), C₆₋₁₄ aryloptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B or heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B, w is an integer of 1 to3, and Y is (1′) a single bond, (2′) C₁₋₆ alkylene, (3′) C₂₋₆alkenylene, (4′) —(CH₂)_(m)—O—(CH₂)_(n)—, (hereinafter m and n are eachindependently 0 or an integer of 1 to 6), (5′) —CO—, (6′)—CO₂—(CH₂)_(n)—, (7′) —CONH—(CH₂)_(n)—NH—, (8′) —NHCO₂—, (9′) —NHCONH—,(10′) —O—(CH₂)_(n)—CO—, (11′) —O—(CH₂)_(n)—O—, (12′) —SO₂—, (13′)—(CH₂)_(m)—NR^(a12)—(CH₂)_(n)— wherein R^(a12) is (1″) hydrogen atom,(2″) optionally substituted C₁₋₆ alkyl (as defined above), (3″) C₆₋₁₄aryl C₁₋₆ alkyl optionally substituted by 1 to 5 substituent(s) selectedfrom the above group B, (4″) C₆₋₁₄ aryl optionally substituted by 1 to 5substituent(s) selected from the above group B, (5″) —COR^(b5)  whereinR^(b5) is hydrogen atom, optionally substituted C₁₋₆ alkyl (as definedabove), C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the above group B or C₆₋₁₄ aryl C₁₋₆ alkyl optionallysubstituted by 1 to 5 substituent(s) selected from the above group B,(6″) —COOR^(b5) (R^(b5) is as defined above) or (7″) —SO₂R^(b5) (R^(b5)is as defined above), (14′) —NR^(a12)CO— (R^(a12) is as defined above),(15′) —CONR^(a13) —(CH₂)_(n)— wherein R^(a13) is hydrogen atom,optionally substituted C₁₋₆ alkyl (as defined above) or C₆₋₁₄ aryl C₁₋₆alkyl optionally substituted by 1 to 5 substituent(s) selected from theabove group B, (16′) —CONH—CHR^(a14)— wherein R^(a14) is C₆₋₁₄ aryloptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B, (17′) —O—(CH₂)_(m)—CR^(a15)R^(a16)—(CH₂)_(n)— wherein R^(a15)and R^(a16) are each independently (1″) hydrogen atom, (2″) carboxyl,(3″) C₁₋₆ alkyl, (4″) —OR^(b6) wherein R^(b6) is C₁₋₆ alkyl or C₆₋₁₄aryl C₁₋₆ alkyl, or (5″) —NHR^(b7) wherein R^(b7) is hydrogen atom, C₁₋₆alkyl, C₁₋₆ alkanoyl or C₆₋₁₄ aryl C₁₋₆ alkyloxycarbonyl, or R^(a15) isoptionally

wherein n′, ring B′, Z′ and w′ are the same as the above-mentioned n,ring B, Z and w, respectively, and may be the same as or different fromthe respective counterparts, (18′) —(CH₂)_(n)—NR^(a12)—CHR^(a15)—(R^(a12) and R^(a15) are each as defined above), (19′) —NR^(a17) SO₂—wherein R^(a17) is hydrogen atom or C₁₋₆ alkyl or (20′)—S(O)_(e)—(CH₂)_(m)—CR^(a15)R^(a16)—(CH₂)_(n)— (e is 0, 1 or 2, R^(a15)and R^(a16) are each as defined above).
 30. The therapeutic agent ofclaim 29, wherein 1 to 4 of the G¹, G², G³, G⁴, G⁵, G⁶, G⁷, G⁸ and G⁹is(are) a nitrogen atom.
 31. The therapeutic agent of claim 30, whereinG² is C(—R²) and G⁶ is a carbon atom.
 32. The therapeutic agent of claim30, wherein G⁵ is a nitrogen atom.
 33. The therapeutic agent of claim29, wherein, in formula [I], the moiety

is a fused ring selected from


34. The therapeutic agent of claim 33, wherein, in formula [I], themoiety

is a fused ring selected from


35. The therapeutic agent of claim 34, which comprises a fused ringcompound of the following formula [I-1]

wherein each symbol is as defined in claim 29, or a pharmaceuticallyacceptable salt thereof as an active ingredient.
 36. The therapeuticagent of claim 34, which comprises a fused ring compound of thefollowing formula [I-2]

wherein each symbol is as defined in claim 29, or a pharmaceuticallyacceptable salt thereof as an active ingredient.
 37. The therapeuticagent of claim 34, which comprises a fused ring compound of thefollowing formula [I-3]

wherein each symbol is as defined in claim 29, or a pharmaceuticallyacceptable salt thereof as an active ingredient.
 38. The therapeuticagent of claim 34, which comprises a fused ring compound of thefollowing formula [I-4]

wherein each symbol is as defined in claim 29, or a pharmaceuticallyacceptable salt thereof as an active ingredient.
 39. The therapeuticagent of claim 29, wherein at least one of R¹, R², R³ and R⁴ iscarboxyl, —COOR^(a1), —CONR^(a2)R^(a3) or —SO₂R^(a7) wherein R^(a1),R^(a2), R^(a3) and R^(a7) are as defined in claim
 29. 40. Thetherapeutic agent of claim 29, wherein the ring Cy is cyclopentyl,cyclohexyl, cycloheptyl or tetrahydrothiopyranyl.
 41. The therapeuticagent of claim 29, wherein the ring A is C₆₋₁₄ aryl.
 42. A fused ringcompound of the following formula [II]

wherein the moiety

is a fused ring selected from

wherein R¹, R², R³ and R⁴ are each independently, (1) hydrogen atom, (2)C₁₋₆ alkanoyl, (3) carboxyl, (4) cyano, (5) nitro, (6) C₁₋₆ alkyloptionally substituted by 1 to 3 substituent(s) selected from thefollowing group A, group A; halogen atom, hydroxyl group, carboxyl,amino, C₁₋₆ alkoxy, C₁₋₆ alkoxy C₁₋₆ alkoxy, C₁₋₆ alkoxycarbonyl andC₁₋₆ alkylamino, (7) —COOR^(a1) wherein R^(a1) is optionally substitutedC₁₋₆ alkyl (as defined above), C₆₋₁₄ aryl C₁₋₆ alkyl optionallysubstituted by 1 to 5 substituent(s) selected from the following group Bor glucuronic acid residue, group B; halogen atom, cyano, nitro, C₁₋₆alkyl, halogenated C₁₋₆ alkyl, C₁₋₆ alkanoyl, (CH₂)_(r)—COOR^(b1),—(CH₂)_(r)—CONR^(b1)R^(b2), —(CH₂)_(r)—NR^(b1)R^(b2),—(CH₂)_(r)—NR^(b1)—COR^(b2), —(CH₂)_(r)—NHSO₂R^(b1), —(CH₂)_(r)—OR^(b1),—(CH₂)_(r)—SR^(b1), —(CH₂)_(r)—SO₂R^(b1) and —(CH₂)_(r)—SO₂NR^(b1)R^(b2)wherein R^(b1) and R^(b2) are each independently hydrogen atom or C₁₋₆alkyl and r is 0 or an 5 integer of 1 to 6, (8) —CONR^(a2)R^(a1) whereinR^(a2) and R^(a3) are each independently hydrogen atom, C₁₋₆ alkoxy oroptionally substituted C₁₋₆ alkyl (as defined above), (9)—C(═NR^(a4))NH₂ wherein R^(a4) is hydrogen atom or hydroxyl group, (10)—NHR^(a5) wherein R^(a5) is hydrogen atom, C₁₋₆ alkanoyl or C₁₋₆alkylsulfonyl, (11) —OR^(a6) wherein R^(a6) is hydrogen atom oroptionally substituted C₁₋₆ alkyl (as defined above), (12) —SO₂R^(a7)wherein R^(a7) is hydroxyl group, amino, C₁₋₆ alkyl or C₁₋₆ alkylamino,(13) —P(═O) (OR^(a31))₂ wherein R^(a31) is hydrogen atom, optionallysubstituted C₁₋₆ alkyl (as defined above) or C₆₋₁₄ aryl C₁₋₆ alkyloptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B, or (14) heterocyclic group having 1 to 4 heteroatom(s) selectedfrom an oxygen atom, a nitrogen atom and a sulfur atom, and R⁷ ishydrogen atom or optionally substitute C₁₋₆ alkyl (as defined above),ring Cy′ is (1) C₃₋₈ cycloalkyl optionally substituted by 1 to 5substituent(s) selected from the following group C, group C; hydroxylgroup, halogen atom, C₁₋₆ alkyl and C₁₋₆ alkoxy, or

wherein u and v are each independently an integer of 1 to 3, ring A′ isa group selected from a group consisting of phenyl, pyridyl, pyrazinyl,pyrimidinyl, pyridazinyl, cyclohexyl, cyclohexenyl, furyl and thienyl,R⁵ and R⁶ are each independently (1) hydrogen atom, (2) halogen atom,(3) optionally substituted C₁₋₆ alkyl (as defined above) or (4) hydroxylgroup ring B is (1) C₆₋₁₄ aryl, (2) C₃₋₈ cycloalkyl or (3) heterocyclicgroup having 1 to 4 heteroatom(s) selected  from an oxygen atom, anitrogen atom and a sulfur atom, each Z is independently (1) a groupselected from the following group D, (2) C₆₋₁₄ aryl optionallysubstituted by 1 to 5 substituent(s) selected from the following groupD, (3) C₃₋₈ cycloalkyl optionally substituted by 1 to 5 substituent(s)selected from the following group D, (4) C₆₋₁₄ aryl C₁₋₆ alkyloptionally substituted b)y 1 to 5 substituent(s) selected from thefollowing group D, (5) heterocyclic group optionally substituted by 1 to5 substituent(s) selected from the following group D wherein theheterocyclic group has 1 to 4 heteroatom(s) selected from an oxygenatom, a nitrogen atom and a sulfur atom, or (6) heterocycle C₁₋₆ alkyloptionally substituted by 1 to 5 substituent(s) selected from thefollowing group D wherein the heterocycle C₁₋₆ alkyl is C₁₋₆ alkylsubstituted by heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the group D, as defined above, group D: (a)hydrogen atom, (b) halogen atom, (c) cyano, (d) nitro, (e) optionallysubstituted C₁₋₆ alkyl (as defined above), (f) —(CH₂)_(t)—COR^(a18),(hereinafter each t means independently 0 or an integer of 1 to 6),wherein R^(a18) is (1′) optionally substituted C₁₋₆ alkyl (as definedabove), (2′) C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s)selected from the above group B or (3′) heterocyclic group optionallysubstituted by 1 to 5 substituent(s) selected from the above group B wherein the heterocyclic group has 1 to 4 heteroatom(s) selected froman oxygen atom, a nitrogen atom and a sulfur atom, (g)—(CH₂)_(t)—COR^(a19) wherein R^(a19) is hydrogen atom, optionallysubstituted C₁₋₆ alkyl (as defined above) or C₆₋₁₄ aryl C₁₋₆ alkyloptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B, (h) —(CH₂)_(t)—CONR^(a27)R^(a28) wherein R^(a27) and R^(a28)are each independently, (1″) hydrogen atom, (2″) optionally substitutedC₁₋₆ alkyl (as defined above), (3″) C₆₋₁₄ aryl optionally substituted by1 to 5 substituent(s) selected from the above group B, (4″) C₆₋₁₄ arylC₁₋₆ alkyl optionally substituted by 1 to 5 substituent(s) selected fromthe above group B, (5″) heterocyclic group optionally substituted by 1to 5 substituent(s) selected from the above group B, (6″) heterocycleC₁₋₆ alkyl optionally substituted by 1 to 5 substituent(s) selected fromthe above group B,  wherein the heterocycle C₁₋₆ alkyl is C₁₋₆ alkylsubstituted by heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B, as defined above, (7″)C₃₋₈ cycloalkyl optionally substituted by 1 to 5 substituent(s) selectedfrom the above group B, (8″) C₃₋₈ cycloalkyl C₁₋₆ alkyl optionallysubstituted by 1 to 5 substituent(s) selected from the above group B,(9″) hydroxyl group or (10″) C₁₋₆ alkoxy, (i) —(CH₂)_(t)—C(═NR^(a33))NH₂wherein R^(a33) is hydrogen atom, C₁₋₆ alkyl, hydroxyl group or C₁₋₆alkoxy, (j) —(CH₂)_(t)OR^(a20) wherein R^(a20) is (1′) hydrogen atom,(2′) optionally substituted C₁₋₆ alkyl (as defined above), (3′)optionally substituted C₂₋₆ alkenyl (as defined above), (4′) C₂₋₆alkynyl optionally substituted by 1 to 3 substituent(s) selected fromthe above group A, (5′) C₆₋₁₄ aryl optionally substituted by 1 to 5substituent(s) selected from, the above group B, (6′) C₆₋₁₄ aryl C₁₋₆alkyl optionally substituted by 1 to 5 substituent(s) selected from theabove group B, (7′) heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B, (8′) heterocycle C₁₋₆alkyl optionally substituted by 1 to 5 substituent(s) selected from theabove group B, (9′) C₃₋₈ cycloalkyl optionally substituted by 1 to 5substituent(s) selected from the above group B, or (10′) C₃₋₈ cycloalkylC₁₋₆ alkyl optionally substituted by 1 to 5 substituent(s) selected fromthe above group B, (k) —(CH₂)_(t)—O—(CH₂)_(p)—COR^(a21) wherein R^(a21)is amino, C₁₋₆ alkylamino or heterocyclic group optionally substitutedby 1 to 5 substituent(s) selected from the above group B, and p is 0 oran integer of 1 to 6, (l) —(CH₂)_(t)—NR^(a22)R^(a23) wherein R^(a22) andR^(a23) are each independently (1′) hydrogen atom, (2′) optionallysubstituted C₁₋₆ alkyl (as defined above), (3′) C₆₋₁₄ aryl optionallysubstituted by 1 to 5 substituent(s) selected from the above group B,(4′) C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B, (5′) heterocycle C₁₋₆alkyl optionally substituted by 1 to 5 substituent(s) selected from theabove group B or (6′) heterocyclic group optionally substituted by 1 to5 substituent(s) selected from the above group B, (m)—(CH₂)_(t)—NR^(a29)CO—R^(a24) wherein R^(a29) is hydrogen atom, C₁₋₆alkyl or C₁₋₆ alkanoyl, and R^(a24) is (1′) amino, (2′) C₁₋₆ alkylamino,(3′) optionally substituted C₁₋₆ alkyl (as defined above), (4′) C₆₋₁₄aryl optionally substituted by 1 to 5 substituent(s) selected from theabove group B, (5′) heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B, or (6′) heterocycle C₁₋₆alkyl optionally substituted by 1 to 5 substituent(s) selected from theabove group B, (n) —(CH₂)_(t)—NR^(a29)SO₂—R^(a25) wherein R^(a29) is asdefined above, and R^(a25) is hydrogen atom, optionally substituted C₁₋₆alkyl (as defined above), C₆₋₁₄ aryl optionally substituted by 1 to 5substituent(s) selected from the above group B or heterocyclic groupoptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B, (o) —(CH₂)_(t)—S(O)_(q)—R^(a25) wherein R^(a25) is as definedabove, arid q is 0, 1 or 2, (p) —(CH₂)_(t)—SO₂—NHR^(a26) wherein R^(a26)is hydrogen atom, optionally substituted C₁₋₆ alkyl (as defined above),C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s) selected fromthe above group B or heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B, and (q) heterocyclicgroup having 1 to 4 heteroatom(s) selected from an oxygen atom, anitrogen atom and a sulfur atom, w is an integer of 1 to 3, and Y is (1)a single bond, (2) C₁₋₆ alkylene, (3) C₂₋₆ alkenylene, (4)—(CH₂)_(m)—O—(CH₂)_(n)—, (hereinafter m and n are each independently 0or an integer of 1 to 6), (5) —CO—, (6) —CO₂—(CH₂)_(n)—, (7)—CONH—(CH₂)_(n)—NH—, (8) —NHCO₂—, (9) —NHCONH—, (10) —O—(CH₂)_(n)—CO—,(11) —O—(CH₂)_(n)—O—, (12) —SO₂—, (13) —(CH₂)_(m)—NR^(a12)—(CH₂)_(n)—wherein R^(a12) is (1′) hydrogen atom, (2′) optionally substituted C₁₋₆alkyl (as defined above), (3′) C₆₋₁₄ aryl C₁₋₆ alkyl optionallysubstituted by 1 to 5 substituent(s) selected from the above group B,(4′) C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s) selectedfrom the above group B, (5′) —COR^(b5) wherein R^(b5) is hydrogen atom,optionally substituted C₁₋₆ alkyl (as defined above), C₆₋₁₄ aryloptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B or C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B, (6′) —COOR^(b5) (R^(b5)is as defined above) or (7′) —SO₂R^(b5) (R^(b5) is as defined above,,(14) —NR^(a12)CO— (R^(a12) is as defined above), (15)—CONR^(a13)—(CH₂)_(n)— wherein R^(a13) is hydrogen atom, optionallysubstituted C₁₋₆ alkyl (as defined above) or C₆₋₁₄ aryl C₁₋₆ alkyloptionally substituted by 1 to 5 substituent(s) selected front the abovegroup B, (16) —CONH—CHR^(a14)— wherein R^(a14) is C₆₋₁₄ aryl optionallysubstituted by 1 to 5 substituent(s) selected from the above group B,(17) —O—(CH₂)_(m)—CR^(a15)R^(a16)—(CH₂)_(n)— wherein R^(a15) and R^(a16)are each independently (1′) hydrogen atom, (2′) carboxyl, (3′) C₁₋₆alkyl, (4′) —OR^(b6) wherein R^(b6) is C₁₋₆ alkyl or C₆₋₁₄ aryl C₁₋₆alkyl, or (5′) —NHR^(b7) wherein R^(b7) is hydrogen atom, C₁₋₆ alkyl,C₁₋₆ alkanoyl or C₆₋₁₄ aryl C₁₋₆ alkyloxycarbonyl, or R^(a15) isoptionally

wherein n′, ring B′, Z′ and w′ are the same as the above-mentioned n,ring B, Z and w, respectively, and may be the same as or different fromthe respective counterparts, (18) —(CH₂)_(n)NR^(a12)—CHR^(a15)— (R^(a12)and R^(a15) are each as defined above), (19) —NR^(a17)SO₂— whereinR^(a17) is hydrogen atom or C₁₋₆ alkyl, (20)—S(O)_(e)—(CH₂)_(m)—CR^(a15)R^(a16)—(CH₂)_(n)— (e is 0, 1 or 2, R^(a15)and R^(a16) are each as defined above), or (21)—(CH₂)_(m)—CR^(a15)R^(a16)—(CH₂)_(n)— (R^(a15) and R^(a16) are each asdefined above), or a pharmaceutically acceptable salt thereof.
 43. Thefused ring compound of claim 42, which is represented by the followingformula [II-1]

wherein each symbol is as defined in claim 42, or a pharmaceuticallyacceptable salt thereof.
 44. The fused ring compound of claim 42, whichis represented by the following formula [II-2]

wherein each symbol is as defined in claim 42, or a pharmaceuticallyacceptable salt thereof.
 45. The fused ring compound of claim 42, whichis represented by the following formula [II-3]

wherein each symbol is as defined in claim 42, or a pharmaceuticallyacceptable salt thereof.
 46. The fused ring compound of claim 42, whichis represented by the following formula [II-4]

wherein each symbol is as defined in claim 42, or a pharmaceuticallyacceptable salt thereof.
 47. The fused ring compound of claim 42,wherein at least one of R¹, R², R³ and R⁴ is carboxyl, —COOR^(a1),—CONR^(a2)R^(a3), —SO₂R^(a7) (wherein R^(a1), R^(a2), R^(a3) and R^(a7)are as defined in claim 42),

or a pharmaceutically acceptable salt thereof.
 48. The fused ringcompound of claim 47, wherein at least one of R¹, R², R³ and R⁴ iscarboxyl, —COOR^(a1) or —SO₂R^(a7) wherein R^(a1) and R^(a7) are asdefined in claim 42, or a pharmaceutically acceptable salt thereof. 49.The fused ring compound of claim 48, wherein at least one of R¹, R², R³and R⁴ is carboxyl or —COOR^(a1) wherein R^(a1) is as defined in claim42, or a pharmaceutically acceptable salt thereof.
 50. The fused ringcompound of claim 49, wherein R² is carboxyl and R¹, R³ and R⁴ arehydrogen atoms, or a pharmaceutically acceptable salt thereof.
 51. Thefused ring compound of claim 42, wherein at least one of R¹, R², R³ andR⁴ is carboxyl or —COOR^(a1) wherein R^(a1) is glucuronic acid residue,or a pharmaceutically acceptable salt thereof.
 52. The fused ringcompound of claim 42, wherein at least one of R¹, R², R³ and R⁴ isheterocyclic group having 1 to 4 heteroatom(s) selected from an oxygenatom, a nitrogen atom and a sulfur atom, or a pharmaceuticallyacceptable salt thereof.
 53. The fused ring compound of claim 42,wherein the ring Cy′ is cyclopentyl, cyclohexyl, cycloheptyl ortetrahydrothiopyranyl, or a pharmaceutically acceptable salt thereof.54. The fused ring compound of claim 42, wherein the ring Cy′ iscyclopentyl, cyclohexyl or cycloheptyl, or a pharmaceutically acceptablesalt thereof.
 55. The fused ring compound of claim 42, wherein the ringCy′ is

wherein each symbol is as defined in claim 42, or a pharmaceuticallyacceptable salt thereof.
 56. The fused ring compound of claim 42,wherein the ring A′ is phenyl, pyridyl, pyrazinyl, pyrimidinyl orpyridazinyl, or a pharmaceutically acceptable salt thereof.
 57. Thefused ring compound of claim 56, wherein the ring A′ is phenyl orpyridyl, or a pharmaceutically acceptable salt thereof.
 58. The fusedring compound of claim 57, wherein the ring A′ is phenyl, or apharmaceutically acceptable salt thereof.
 59. The fused ring compound ofclaim 42, wherein at least one substituent optionaly substituted bygroup A is a substituent substituted by C₁₋₆ alkoxy C₁₋₆ alkoxy, or apharmaceutically acceptable salt thereof.
 60. The fused ring compound ofclaim 42, wherein the Y is —(CH₂)_(m)—O—(CH₂)_(n)—, —NHCO₂—,—CONH—CHR^(a14)—, —(CH₂)_(m)—NR^(a12)—(CH₂)_(n)—,—CONR^(a13)—(CH₂)_(n)—, —O—(CH₂ )_(m)CR^(a15)R^(a16)—(CH₂)_(n)— or—(CH₂)_(n)—NR^(a12)—CHR^(a15)— (wherein each symbol is as defined inclaim 42), or a pharmaceutically acceptable salt thereof.
 61. The fusedring compound of claim 42, wherein the Y is —(CH₂)_(m)—O—(CH₂)_(n)— or—O—(CH₂)_(m)CR^(a15)R^(a6)—(CH₂)_(n)— (wherein each symbol is as definedin claim 42), or a pharmaceutically acceptable salt thereof.
 62. Thefused ring compound of claim 61, wherein the Y is—(CH₂)_(m)—O—(CH₂)_(n)— wherein each symbol is as defined in claim 42,or a pharmaceutically acceptable salt thereof.
 63. The fused ringcompound of claim 42, wherein the Y is—(CH₂)_(m)—CR^(a15)R^(a16)—(CH₂)_(n)— (wherein each symbol is as definedin claim 42), or a pharmaceutically acceptable salt thereof.
 64. Thefused ring compound of claim 42, wherein the R² is carboxyl, R¹, R³ andR⁴ are hydrogen atoms, the ring Cy′ is cyclopentyl, cyclohexyl orcycloheptyl, and the ring A′ is phenyl, or a pharmaceutically acceptablesalt thereof.
 65. The fused ring compound of claim 42, wherein at leastone group represented by Z is heterocycle C₁₋₆ alkyl optionallysubstituted by 1 to 5 substituent(s) selected from the group D, or apharmaceutically acceptable salt thereof.
 66. The fused ring compound ofclaim 42, wherein at least one group represented by Z is heterocyclicgroup optionally substituted by 1 to 5 substituent(s) selected from thegroup D, wherein said heterocyclic group is selected from the followinggroups:

wherein E¹ is an oxygen atom, a sulfur atom or N(—R^(a35)), E² is anoxygen atom, CH₂ or N(—R^(a35)), E³ is an oxygen atom or a sulfur atom,wherein each R^(a35) is independently hydrogen atom or C₁₋₆ alkyl, f isan integer of 1 to 3, and h and h′ are the same or different and each isan integer of 1 to 3, or a pharmaceutically acceptable salt thereof. 67.The fused ring compound of claim 66, wherein at least one grouprepresented by Z is heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the group D, wherein said heterocyclicgroup is selected from the following groups:

wherein each symbol is as defined in claim 66, or a pharmaceuticallyacceptable salt thereof.
 68. The fused ring compound of claim 42,wherein at least one group represented by group D is—(CH₂)_(t)—CONR^(a27)R^(a28) wherein each symbol is as defined in claim42, and at least one of R^(a27) and R^(a28) is C₁₋₆ alkoxy, or apharmaceutically acceptable salt thereof.
 69. The fused ring compound ofclaim 42, wherein at least one group represented by group D is—(CH₂)_(t)—C(═NR^(a33))NH₂ wherein each symbol is as defined in claim42, and R^(a33) is hydroxyl croup or C₁₋₆ alkoxy, or a pharmaceuticallyacceptable salt thereof.
 70. The fused ring compound of claim 42,wherein at least one group represented by group D is—(CH₂)_(t)—O—(CH₂)_(p)—COR^(a21) wherein each symbol is as defined inclaim 42, and R^(a21) is amino, or a pharmaceutically acceptable saltthereof.
 71. The fused ring compound of claim 42, wherein at least onegroup represented by group D is —(CH₂)_(t)—NR^(a29)CO—R^(a24) whereineach symbol is as defined in claim 42, and R^(a24) is amino or C₁₋₆alkylamino, or a pharmaceutically acceptable salt thereof.
 72. The fusedring compound of claim 42, wherein at least one group represented bygroup D is —(CH₂)_(t)—NR^(a22)R^(a23) wherein each symbol is as definedin claim 42, and at least one of R^(a22) and R^(a23) is heterocyclicgroup optionally substituted by 1 to 5 substituent(s) selected from thegroup B, or a pharmaceutically acceptable salt thereof.
 73. The fusedring compound of claim 42, wherein at least one group represented bygroup D is heterocyclic group having 1 to 4 heteroatom(s) selected froman oxygen atom, a nitrogen atom and a sulfur atom, or a pharmaceuticallyacceptable salt thereof.
 74. The fused ring compound of claim 42, whichis represented by the following formula [II]

wherein the moiety

is a fused ring selected from

wherein R¹, R², R³ and R⁴ are each independently, (1) hydrogen atom, (2)C₁₋₆ alkanoyl, (3) carboxyl, (4) cyano, (5) nitro, (6) C₁₋₆ alkyloptionally substituted by 1 to 3 substituent(s) selected from thefollowing group A, group A; halogen atom, hydroxyl group, carboxyl,amino, C₁₋₆ alkoxy, C₁₋₆ alkoxycarbonyl and C₁₋₆ alkylamino, (7)—COOR^(a1) wherein R^(a1) is optionally substituted C₁₋₆ alkyl (asdefined above) or C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the following group B, group B; halogenatom, cyano, nitro, C₁₋₆ alkyl, halogenated C₁₋₆ alkyl, C₁₋₆ alkanoyl,—(CH₂)_(r)—COOR^(b1), —(CH₂)_(r)—CONR^(b1)R^(b2),—(CH₂)_(r)—NR^(b1)R^(b2), —(CH₂)_(r)NR^(b1)—COR^(b2),—(CH₂)_(r)—NHSO₂R^(b1), —(CH₂)_(r)—OR^(b1), —(CH₂)_(r)—SR^(b1),—(CH₂)_(r)—SO₂R^(b1) and —(CH₂)_(r)—SO₂NR^(b1)R^(b2) wherein R^(b1) andR^(b2) are each independently hydrogen atom or C₁₋₆ alkyl and r is 0 oran integer of 1 to 6, (8) —CONR^(a2)R^(a3) wherein R^(a2) and R^(a3) areeach independently hydrogen atom, C₁₋₆ alkoxy or optionally substitutedC₁₋₆ alkyl (as defined above), (9) —C(═NR )NH₂ wherein R^(a4) ishydrogen atom or hydroxyl group, (10) —NHR^(a5) wherein R^(a5) ishydrogen atom, C₁₋₆ alkanoyl or C₁₋₆ alkylsulfonyl, (11) —OR^(a6)wherein R^(a6) is hydrogen atom or optionally substituted C₁₋₆ alkyl (asdefined above), (12) —SO₂R^(a7) wherein R^(a7) is hydroxyl group, amino,C₁₋₆ alkyl or C₁₋₆ alkylamino or (13) —P(═O)(OR^(a31))₂ wherein R^(a31)is hydrogen atom, optionally substituted C₁₋₆ alkyl (as defined above)or C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5 substituent(s)selected from the above group B, and R⁷ is hydrogen atom or optionallysubstituted C₁₋₆ alkyl (as defined above), ring Cy′ is (1) C₃₋₈cycloalkyl optionally substituted by 1 to 5 substituent(s) selected fromthe following group C, group C; hydroxyl group, halogen atom, C₁₋₆ alkyland C₁₋₆ alkoxy, or

wherein u and v are each independently an integer of 1 to 3, ring A′ isa group selected from a group consisting of phenyl, pyridyl, pyrazinyl,pyrimidinyl, pyridazinyl, cyclohexyl, cyclohexenyl, furyl and thienyl,R^(5′) and R^(6′) are each independently (1) hydrogen atom, (2) halogenatom, (3) optionally substituted C₁₋₆ alkyl (as defined above) or (4)hydroxyl group ring B is (1) C₆₋₁₄ aryl, (2) C₃₋₈ cycloalkyl or (3)heterocyclic group having 1 to 4 heteroatom(s) selected from an oxygenatom, a nitrogen atom and a sulfur atom, each Z is independently (1) agroup selected from the following group D, (2) C₆₋₁₄ aryl optionallysubstituted by 1 to 5 substituent(s) selected from the following groupD, (3) C₃₋₈ cycloalkyl optionally substituted by 1 to 5 substituent(s)selected from the following group D, (4) C₆₋₁₄ aryl C₁₋₆ alkyloptionally substituted by 1 to 5 substituent(s) selected from thefollowing group D or (5) heterocyclic group optionally substituted by 1to 5 substituent(s) selected from the following group D wherein theheterocyclic group has 1 to 4 heteroatom(s) selected from an oxygenatom, a nitrogen atom and a sulfur atom, group D: (a) hydrogen atom, (b)halogen atom, (c) cyano, (d) nitro, (e) optionally substituted C₁₋₆alkyl (as defined above), (f) —(CH₂)_(t)—COR^(a18), (hereinafter each tmeans independently 0 or an integer of 1 to 6), wherein R^(a18) is (1′)optionally substituted C₁₋₆ alkyl (as defined above), (2′) C₆₋₁₄ aryloptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B or (3′) heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B  wherein the heterocyclicgroup has 1 to 4 heteroatom(s) selected from an oxygen atom, a nitrogenatom and a sulfur atom, (g) —(CH₂)_(t)—COOR^(a19) wherein R^(a19) ishydrogen atom, optionally substituted C₁₋₆ alkyl (as defined above) orC₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5 substituent(s)selected from the above group B, (h) —(CH₂)_(t)—CONR^(a27)R^(a28)wherein R^(a27) and R^(a28) are each independently, (1″) hydrogen atom,(2″) optionally substituted C₁₋₆ alkyl (as defined above), (3″) C₆₋₁₄aryl optionally substituted by 1 to 5 substituent(s) selected from theabove group B, (4″) C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to5 substituent(s) selected from the above group B, (5″) heterocyclicgroup optionally substituted by 1 to 5 substituent(s) selected from theabove group B, (6″) heterocycle C₁₋₆ alkyl optionally substituted by 1to 5 substituent(s) selected from the above group B,  wherein theheterocycle C₁₋₆ alkyl is C₁₋₆ alkyl substituted by heterocyclic groupoptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B, as defined above, (7″) C₃₋₈ cycloalkyl optionally substitutedby 1 to 5 substituent(s) selected from the above group B, or (8″) C₃₋₈cycloalkyl C₁₋₆ alkyl optionally substituted by 1 to 5 substituent(s)selected from the above group B, (i) —(CH₂)_(t)—C(═NR^(a33))NH₂ whereinR^(a33) is hydrogen atom or C₁₋₆ alkyl, (j) —(CH₂)_(t)—OR^(a20) whereinR^(a20) is (1′) hydrogen atom, (2′) optionally substituted C₁₋₆ alkyl(as defined above), (3′) optionally substituted C₂₋₆ alkenyl (as definedabove), (4′) C₂₋₆ alkynyl optionally substituted by 1 to 3substituent(s) selected from the above group A, (5′) C₆₋₁₄ aryloptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B, (6′) C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B, (7′) heterocyclic groupoptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B, (8′) heterocycle C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B, (9′) C₃₋₈ cycloalkyloptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B, or (10′) C₃₋₈ cycloalkyl C₁₋₆ alkyl optionally substituted by 1to 5 substituent(s) selected from the above group B, (k)—(CH₂)_(t)—O—(CH₂)_(p)—COR^(a21) wherein R^(a21) is C₁₋₆ alkylamino orheterocyclic group optionally substituted by 1 to 5 substituent(s)selected from the above group B, and p is 0 or an integer of 1 to 6, (l)—(CH₂)_(t)—NR^(a22)R^(a23) wherein R^(a22) and R^(a23) are eachindependently (1′) hydrogen atom, (2′) optionally substituted C₁₋₆ alkyl(as defined above), (3′) C₆₋₁₄ aryl optionally substituted by 1 to 5substituent(s) selected from the above group B, (4′) C₆₋₁₄ aryl C₁₋₆alkyl optionally substituted by 1 to 5 substituent(s) selected from theabove group B or (5′) heterocycle C₁₋₆ alkyl optionally substituted by 1to 5 substituent(s) selected from the above group B, (m)—(CH₂)_(t)—NR^(a29)CO—R^(a24) wherein R^(a29) is hydrogen atom, C₁₋₆alkyl or C₁₋₆ alkanoyl, R^(a24) is optionally substituted C₁₋₆ alkyl (asdefined above), C₆₋₁₄ aryl optionally substituted by 1 to 5substituent(s) selected from the above group B or heterocyclic groupoptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B, (n) —(CH₂)_(t)—NHSO₂—R^(a25) wherein R^(a25) is hydrogen atom,optionally substituted C₁₋₆ alkyl (as defined above), C₆₋₁₄ aryloptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B or heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B, (o)—(CH₂)_(t)—S(O)_(q)—R^(a25) wherein R^(a25) is as defined above, and qis 0, 1 or 2, and (p) —(CH₂)_(t)—SO₂—NHR^(a26) wherein R^(a26) ishydrogen atom, optionally substituted C₁₋₆ alkyl (as defined above),C₆₋₁₄ aryl optionally substituted b, 1 to 5 substituent(s) selected fromthe above group B or heterocyclic group optionally substituted by 1 to 5substituent(s) selected from the above group B, w is an integer of 1 to3, and Y is (1) a single bond, (2) C₁₋₆ alkylene, (3) C₂₋₆ alkenylene,(4) —(CH₂)_(m)—O—(CH₂)_(n)—, (hereinafter m and n are each independently0 or an integer of 1 to 6), (5) —CO—, (6) —CO₂—(CH₂)_(n)—, (7)—CONH—(CH₂)_(n)—NH—, (8) —NHCO₂—, (9) —NHCONH—, (10) —O—(CH₂)_(n)—CO—,(11) —O—(CH₂)_(n)—O—, (12) —SO₂—, (13) —(CH₂)_(m)—NR^(a12)—(CH₂)_(n)—wherein R^(a12) is (1′) hydrogen atom, (2′) optionally substituted C₁₋₆alkyl (as defined above), (3′) C₆₋₁₄ aryl C₁₋₆ alkyl optionallysubstituted by 1 to 5 substituent(s) selected from the above group B,(4′) C₆₋₁₄ aryl optionally substituted by 1 to 5 substituent(s) selectedfrom the above group B, (5′) —COR^(b5) wherein R^(b5) is hydrogen atom,optionally substituted C₁₋₆ alkyl (as defined above), C₆₋₁₄ aryloptionally -substituted by 1 to 5 substituent(s) selected from the abovegroup B or C₆₋₁₄ aryl C₁₋₆ alkyl optionally substituted by 1 to 5substituent(s) selected from the above group B, (6′) —COOR^(b5) (R^(b5)is as defined above) or (7′) —SO₂R^(b5) (R^(b5) is as defined above),(14) —NR^(a12)CO— (R^(a12) is as defined above), (15)—CONR^(a13)—(CH₂)_(n)— wherein R^(a13) is hydrogen atom, optionallysubstituted C₁₋₆ alkyl (as defined above) or C₆₋₁₄ aryl C₁₋₆ alkyloptionally substituted by 1 to 5 substituent(s) selected from the abovegroup B, (16) —CONH—CHR^(a14)— wherein R^(a14) is C₆₋₁₄ aryl optionallysubstituted by 1 to 5 substituent(s) selected from the above group B,(17) —O—(CH₂)_(m)—CR^(a15)R^(a16)—(CH₂)_(n)— wherein R^(a15) and R^(a16)are each independently (1′) hydrogen atom, (2′) carboxyl, (3′) C₁₋₆alkyl, (4′) —OR^(b6) wherein R^(b6) is C₁₋₆ alkyl or C₆₋₁₄ aryl C₁₋₆alkyl, or (5′) —NHR^(b7) wherein R^(b7) is hydrogen atom, C₁₋₆ alkyl,C₁₋₆ alkanoyl or C₆₋₁₄ aryl C₁₋₆ alkyloxycarbonyl, or R^(a15) isoptionally

wherein n′, ring B′, Z′ and w′ are the same as the above-mentioned n,ring B, Z and w, respectively, and may be the same as or different fromthe respective counterparts, (18) —(CH₂)_(n)—NR^(a12)—CHR^(a15)—(R^(a12) and R^(a15) are each as defined above), (19 ) —NR^(a17)SO₂—wherein R^(a17) is hydrogen atom or C₁₋₆ alkyl or (20)—S(O)_(e)—(CH₂)_(m)—CR^(a15)R^(a16)—(CH₂)_(n)— (e is 0, 1 or 2, R^(a15)and R^(a16) are each as defined above), or a pharmaceutically acceptablesalt thereof.
 75. The fused ring compound of claim 74, which isrepresented by the following formula [II-1]

wherein each symbol is as defined in claim 74, or a pharmaceuticallyacceptable salt thereof.
 76. The fused ring compound of claim 74, whichis represented by the following formula [II-2]

wherein each symbol is as defined in claim 74, or a pharmaceuticallyacceptable salt thereof.
 77. The fused ring compound of claim 74, whichis represented by the following formula [II-3]

wherein each symbol is as defined in claim 74, or a pharmaceuticallyacceptable salt thereof.
 78. The fused ring compound of claim 74, whichis represented by the following formula [II-4]

wherein each symbol is as defined in claim 74, or a pharmaceuticallyacceptable salt thereof.
 79. The fused ring compound of claim 74,wherein at least one of R¹, R², R³ and R⁴ is carboxyl, —COOR^(a1) or—SO₂R^(a7) wherein R^(a1) and R^(a7) are as defined in claim 74, or apharmaceutically acceptable salt thereof.
 80. The fused ring compound ofclaim 79, wherein at least one of R¹, R², R³ and R⁴ is carboxyl or—COOR^(a1) wherein R^(a1) is as defined in claim 74, or apharmaceutically acceptable salt thereof.
 81. The fused ring compound ofclaim 80, wherein R² is carboxyl and R¹, R³ and R⁴ are hydrogen atoms,or a pharmaceutically acceptable salt thereof.
 82. The fused ringcompound of claim 74, wherein the ring Cy′ is cyclopentyl, cyclohexyl,cycloheptyl or tetrahydrothiopyranyl, or a pharmaceutically acceptablesalt thereof.
 83. The fused ring compound of claim 82, wherein the ringCy′ is cyclopentyl, cyclohexyl or cycloheptyl, or a pharmaceuticallyacceptable salt thereof.
 84. The fused ring compound of claim 74,wherein the ring A′ is phenyl, pyridyl, pyrazinyl, pyrimidinyl orpyridazinyl, or a pharmaceutically acceptable salt thereof.
 85. Thefused ring compound of claim 74, wherein the ring A′ is phenyl orpyridyl, or a pharmaceutically acceptable salt thereof.
 86. The fusedring compound of claim 85, wherein the ring A′ is phenyl, or apharmaceutically acceptable salt thereof.
 87. The fused ring compound ofclaim 74, wherein the Y is —(CH₂)_(m)—O—(CH₂)_(n)—, —NHCO₂—,—CONH—CHR^(a14)—, —(CH₂)_(m)—NR^(a12)—(CH₂)_(n)—,—CONR^(a13)—(CH₂)_(n)—, —O—(CH₂)_(m)—CR^(a15)R^(a16)—(CH₂)_(n)— or—(CH₂)_(n)—NR^(a12)—CHR^(a15)— (wherein each symbol is as defined inclaim 74), or a pharmaceutically acceptable salt thereof.
 88. The fusedring compound of claim 87, wherein the Y is —(CH₂)_(m)—O—(CH₂)_(n)— or—O—(CH₂)_(m)—CR^(a15)R^(a16)—(CH₂)_(n)— (wherein each symbol is asdefined in claim 74), or a pharmaceutically acceptable salt thereof. 89.The fused ring compound of claim 88, wherein the Y is(CH₂)_(m)—O—(CH₂)_(n)— wherein each symbol is as defined in claim 74, ora pharmaceutically acceptable salt thereof.
 90. The fused ring compoundof claim 74, wherein the R′ is carboxyl, R′, R³ and R⁴ are hydrogenatoms, the ring Cy′ is cyclopentyl, cyclohexyl or cycloheptyl, and thering A′ is phenyl, or a pharmaceutically acceptable salt thereof. 91.The fused ring compound of claim 42 or a pharmaceutically acceptablesalt thereof, which is selected from the group consisting of ethyl2-[4-(3-bromophenoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylate,2-[4-(3-bromophenoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid, ethyl2-[4-(2-bromo-5-chlorobenzyloxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylate,ethyl2-{4-[2-(4-chlorophenyl)-5-chlorobenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylate,2-{4-[2-(4-chlorophenyl)-5-chlorobenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid, ethyl2-[4-(2-bromo-5-methoxybenzyloxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylate,ethyl2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylate,2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid, ethyl1-cyclohexyl-2-{4-[(E)-2-phenylvinyl]phenyl}benzimidazole-5-carboxylate,1-cyclohexyl-2-{4-[(E)-2-phenylvinyl]phenyl}benzimidazole-5-carboxylicacid, 2-(4-benzyloxyphenyl)-1-cyclopentylbenzimidazole-5-carboxylicacid, 2-(4-benzyloxyphenyl)-1-cyclopentylbenzimidazole-5-carboxamide,2-(4-benzyloxyphenyl)-5-cyano-1-cyclopentylbenzimidazole,2-(4-benzyloxyphenyl)-1-cyclopentylbenzimidazole-5-carboxamide oxime,ethyl1-cyclohexyl-2-{4-[{4-(4-fluorophenyl)-2-methyl-5-thiazolyl}methoxy]phenyl}benzimidazole-5-carboxylate,1-cyclohexyl-2-{4-[{4-(4-fluorophenyl)-2-methyl-5-thiazolyl}-methoxy]phenyl}benzimidazole-5-carboxylicacid, ethyl2-{4-[bis(3-fluorophenyl)methoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylate,2-{4-[bis(3-fluorophenyl)methoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid, ethyl2-(4-benzoylaminophenyl)-1-cyclopentylbenzimidazole-5-carboxylate,2-(4-benzoylaminophenyl)-1-cyclopentylbenzimidazole-5-carboxylic acid,ethyl2-{4-[3-(3-chlorophenyl)phenoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylate,2-{4-[3-(3-chlorophenyl)phenoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid, ethyl2-[4-(3-acetoxyphenyloxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylate,ethyl1-cyclohexyl-2-[4-(3-hydroxyphenyloxy)phenyl]-benzimidazole-5-carboxylate,ethyl1-cyclohexyl-2-{4-[3-(4-pyridylmethoxy)phenyloxy]phenyl}-benzimidazole-5-carboxylate,1-cyclohexyl-2-{4-[3-(4-pyridylmethoxy)phenyloxy]phenyl}-benzimidazole-5-carboxylicacid, 2-(4-benzyloxyphenyl)-1-cyclopentylbenzimidazole, ethyl2-(4-benzyloxyphenyl)-1-cyclopentylbenzimidazole-5-carboxylate,2-(4-benzyloxyphenyl)-1-cyclopentyl-N,N-dimethylbenzimidazole-5-carboxamide,2-(4-benzyloxyphenyl)-1-cyclopentyl-N-methoxy-N-methylbenzimidazole-5-carboxamide,2-(4-benzyloxyphenyl)-1-cyclopentyl-5-(1-hydroxy-1-methylethyl)-benzimidazole,5-acetyl-2-(4-benzyloxyphenyl)-1-cyclopentylbenzimidazole,2-(4-benzyloxyphenyl)-1-cyclopentyl-N-(2-dimethylaminoethyl)-benzimidazole-5-carboxamidedihydrochloride,2-(4-benzyloxyphenyl)-1-cyclopentyl-5-nitrobenzimidazole,5-amino-2-(4-benzyloxyphenyl)-1-cyclopentylbenzimidazole hydrochloride,5-acetylamino-2-(4-benzyloxyphenyl)-1-cyclopentylbenzimidazole,2-(4-benzyloxyphenyl)-1-cyclopentyl-5-methanesulfonylaminobenzimidazole,5-sulfamoyl-2-(4-benzyloxyphenyl)-1-cyclopentylbenzimidazole,2-[4-(4-tert-butylbenzyloxy)phenyl]-1-cyclopentylbenzimidazole-5-carboxylicacid,2-[4-(4-carboxybenzyloxy)phenyl]-1-cyclopentylbenzimidazole-5-carboxylicacid,2-[4-(4-chlorobenzyloxy)phenyl]-1-cyclopentylbenzimidazole-5-carboxylicacid,2-{4-[(2-chloro-5-thienyl)methoxy]phenyl}-1-cyclopentylbenzimidazole-5-carboxylicacid,1-cyclopentyl-2-[4-(4-trifluoromethylbenzyloxy)phenyl]-benzimidazole-5-carboxylicacid,1-cyclopentyl-2-[4-(4-methoxybenzyloxy)phenyl]benzimidazole-5-carboxylicacid,1-cyclopentyl-2-[4-(4-pyridylmethoxy)phenyl]benzimidazole-5-carboxylicacid hydrochloride,1-cyclopentyl-2-[4-(4-methylbenzyloxy)phenyl]benzimidazole-5-carboxylicacid,1-cyclopentyl-2-{4-[(3,5-dimethyl-4-isoxazolyl)methoxy]phenyl}-benzimidazole-5-carboxylicacid,[2-(4-benzyloxyphenyl)-1-cyclopentylbenzimidazol-5-yl]-carbonylaminoaceticacid,2-[4-(2-chlorobenzyloxy)phenyl]-1-cyclopentylbenzimidazole-5-carboxylicacid,2-[4-(3-chlorobenzyloxy)phenyl]-1-cyclopentylbenzimidazole-5-carboxylicacid, 2-(4-benzyloxyphenyl)-3-cyclopentylbenzimidazole-5-carboxylicacid,2-[4-(benzenesulfonylamino)phenyl]-1-cyclopentylbenzimidazole-5-carboxylicacid,1-cyclopentyl-2-[4-(3,5-dichlorophenylcarbonylamino)phenyl]-benzimidazole-5-carboxylicacid,2-{4-[(4-chlorophenyl)carbonylamino]phenyl}-1-cyclopentylbenzimidazole-5-carboxylicacid,2-{4-[(4-tert-butylphenyl)carbonylamino]phenyl}-1-cyclopentylbenzimidazole-5-carboxylicacid,2-{4-[(4-benzyloxyphenyl)carbonylamino]phenyl}-1-cyclopentylbenzimidazole-5-carboxylicacid,trans-4-[2-(4-benzyloxyphenyl)-5-carboxybenzimidazol-1-yl]cyclohexan-1-ol,trans-1-[2-(4-benzyloxyphenyl)-5-carboxybenzimidazol-1-yl]-4-methoxycyclohexane,2-(4-benzyloxyphenyl)-5-carboxymethyl-1-cyclopentylbenzimidazole,2-[(4-cyclohexylphenyl)carbonylamino]-1-cyclopentylbenzimidazole-5-carboxylicacid,1-cyclopentyl-2-[4-(3,5-dichlorobenzyloxy)phenyl]benzimidazole-5-carboxylicacid,1-cyclopentyl-2-[4-(3,4-dichlorobenzyloxy)phenyl]benzimidazole-5-carboxylicacid,1-cyclopentyl-2-[4-(phenylcarbamoylamino)phenyl]benzimidazole-5-carboxylicacid,1-cyclopentyl-2-[4-(diphenylmethoxy)phenyl]benzimidazole-5-carboxylicacid, 1-cyclopentyl-2-(4-phenethyloxyphenyl)benzimidazole-5-carboxylicacid,trans-1-[2-(4-benzyloxyphenyl)-5-carboxybenzimidazol-1-yl]-4-tert-butylcyclohexane,2-(4-benzyloxyphenyl)-5-carboxymethoxy-1-cyclopentylbenzimidazole,2-(4-benzylaminophenyl)-1-cyclopentylbenzimidazole-5-carboxylic acid,2-[4-(N-benzenesulfonyl-N-methylamino)phenyl]-1-cyclopentylbenzimidazole-5-carboxylicacid,2-[4-(N-benzyl-N-methylamino)phenyl]-1-cyclopentylbenzimidazole-5-carboxylicacid, 1-cyclohexyl-2-(4-phenethylphenyl)benzimidazole-5-carboxylic acid,1-cyclohexyl-2-[4-(3,5-dichlorobenzyloxy)phenyl]benzimidazole-5-carboxylicacid,1-cyclohexyl-2-[4-(diphenylmethoxy)phenyl]benzimidazole-5-carboxylicacid,1-cyclohexyl-2-[4-(3,5-di-tert-butylbenzyloxy)phenyl]-benzimidazole-5-carboxylicacid,2-(4-benzyloxyphenyl)-1-(4-methylcyclohexyl)benzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[2-(2-naphthyl)ethoxy]phenyl}benzimidazole-5-carboxylicacid,1-cyclohexyl-2-[4-(1-naphthyl)methoxyphenyl]benzimidazole-5-carboxylicacid, 1-cyclohexyl-2-[4-(dibenzylamino)phenyl]benzimidazole-5-carboxylicacid,2-[4-(2-biphenylylmethoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid, 2-(4-benzyloxyphenyl)-1-cyclohexylbenzimidazole-5-carboxylic acid,1-cyclohexyl-2-[4-(dibenzylmethoxy)phenyl]benzimidazole-5-carboxylicacid, 2-(4-benzoylmethoxyphenyl)-1-cyclohexylbenzimidazole-5-carboxylicacid,1-cyclohexyl-2-[4-(3,3-diphenylpropyloxy)phenyl]benzimidazole-5-carboxylicacid,2-[4-(3-chloro-6-phenylbenzyloxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[2-(phenoxy)ethoxy]phenyl}benzimidazole-5-carboxylicacid,1-cyclohexyl-2-[4-(3-phenylpropyloxy)phenyl]benzimidazole-5-carboxylicacid,1-cyclohexyl-2-[4-(5-phenylpentyloxy)phenyl]benzimidazole-5-carboxylicacid, 2-(2-benzyloxy-5-pyridyl)-1-cyclohexylbenzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[2-(3,4,5-trimethoxyphenyl)ethoxy]phenyl}-benzimidazole-5-carboxylicacid,2-(4-benzyloxyphenyl)-1-(4,4-dimethylcyclohexyl)benzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[2-(1-naphthyl)ethoxy]phenyl}benzimidazole-5-carboxylicacid,2-[4-(2-benzyloxyphenoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid,2-[4-(3-benzyloxyphenoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid,1-cyclohexyl-2-[4-(2-hydroxyphenoxy)phenyl]benzimidazole-5-carboxylicacid,1-cyclohexyl-2-[4-(3-hydroxyphenoxy)phenyl]benzimidazole-5-carboxylicacid,1-cyclohexyl-2-[4-(2-methoxyphenoxy)phenyl]benzimidazole-5-carboxylicacid,1-cyclohexyl-2-[4-(3-methoxyphenoxy)phenyl]benzimidazole-5-carboxylicacid,1-cyclohexyl-2-[4-(2-propoxyphenoxy)phenyl]benzimidazole-5-carboxylicacid,1-cyclohexyl-2-[4-(3-propoxyphenoxy)phenyl]benzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[2-(3-methyl-2-butenyloxy)phenoxy]phenyl}-benzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[3-(3-methyl-2-butenyloxy)phenoxy]phenyl}-benzimidazole-5-carboxylicacid,1-cyclohexyl-2-[4-(2-isopentyloxyphenoxy)phenyl]benzimidazole-5-carboxylicacid,1-cyclohexyl-2-[4-(3-isopentyloxyphenoxy)phenyl]benzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[2-(10,11-dihydro-5H-dibenzo[b,f]azepin-5-yl)ethoxy]phenyl}benzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[2-(4-trifluoromethylphenyl)benzyloxy]-phenyl}benzimidazole-5-carboxylicacid,2-{4-[bis(4-chlorophenyl)methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[2-(4-methoxyphenyl)ethoxy]phenyl}-benzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[2-(2-methoxyphenyl)ethoxy]phenyl}-benzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[2-(3-methoxyphenyl)ethoxy]phenyl}-benzimidazole-5-carboxylicacid, 2-(4-benzyloxyphenyl)-1-cycloheptylbenzimidazole-5-carboxylicacid,1-cyclohexyl-2-[4-(2-phenethyloxyphenoxy)phenyl]benzimidazole-5-carboxylicacid,1-cyclohexyl-2-[4-(3-phenethyloxyphenoxy)phenyl]benzimidazole-5-carboxylicacid,1-cyclohexyl-2-[4-(2,2-diphenylethoxy)phenyl]benzimidazole-5-carboxylicacid,cis-1-[2-(4-benzyloxyphenyl)-5-carboxybenzimidazol-1-yl]-4-fluorocyclohexane,1-cyclohexyl-2-[4-(2-phenoxyphenoxy)phenyl]benzimidazole-5-carboxylicacid,1-cyclohexyl-2-[4-(3-phenoxyphenoxy)phenyl]benzimidazole-5-carboxylicacid,2-{4-[(2R)-2-benzyloxycarbonylamino-2-phenylethoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,1-cyclohexyl-2-{2-fluoro-4-[2-(4-trifluoromethylphenyl)-benzyloxy]phenyl}benzimidazole-5-carboxylicacid,2-[4-(4-benzyloxyphenoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[bis(4-methylphenyl)methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[bis(4-fluorophenyl)methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,1-cyclohexyl-6-methoxy-2-[4-(3-phenylpropoxy)phenyl]-benzimidazole-5-carboxylicacid,1-cyclohexyl-6-hydroxy-2-[4-(3-phenylpropoxy)phenyl]-benzimidazole-5-carboxylicacid,1-cyclohexyl-6-methyl-2-[4-(3-phenylpropoxy)phenyl]-benzimidazole-5-carboxylicacid,2-{4-[2-(2-benzyloxyphenyl)ethoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[2-(3-benzyloxyphenyl)ethoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-[4-(2-carboxymethyloxyphenoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid,2-[4-(3-carboxymethyloxyphenoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[3-chloro-6-(4-methylphenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[3-chloro-6-(4-methoxyphenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,1-cyclohexyl-2-{2-methyl-4-[2-(4-trifluoromethylphenyl)-benzyloxy]phenyl}benzimidazole-5-carboxylicacid,2-{4-[2-(4-tert-butylphenyl)-5-chlorobenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-(3-chloro-6-phenylbenzyloxy)-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[3-chloro-6-(3,5-dichlorophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[bis(4-fluorophenyl)methoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-(4-benzyloxyphenoxy)-2-chlorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-(4-benzyloxyphenoxy)-2-trifluoromethylphenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[3-chloro-6-(2-trifluoromethylphenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[(2R)-2-amino-2-phenylethoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-[4-(2-biphenylyloxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid,2-[4-(3-biphenylyloxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid, 2-{4-[2-(1-tert-butoxycarbonyl-4-piperidyl)methoxyphenoxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylic acid,2-{4-[3-{(1-tert-butoxycarbonyl-4-piperidyl)methoxy}phenoxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[3-chloro-6-(3,4,5-trimethoxyphenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[2-(2-biphenylyl)ethoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-[4-(2-biphenylylmethoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[2-(4-piperidylmethoxy)phenoxy]phenyl}-benzimidazole-5-carboxylicacid hydrochloride,1-cyclohexyl-2-{4-[3-(4-piperidylmethoxy)phenoxy]phenyl}-benzimidazole-5-carboxylicacid hydrochloride,2-{4-[(2R)-2-acetylamino-2-phenylethoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[3-(4-methyl-3-pentenyloxy)phenoxy]phenyl}-benzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[3-(3-methyl-3-butenyloxy)phenoxy]phenyl}-benzimidazole-5-carboxylicacid,2-{4-[{(2S)-1-benzyl-2-pyrrolidinyl}methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochlorides,2-{4-[3-chloro-6-(4-methylthiophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[3-chloro-6-(4-methanesulfonylphenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[3-chloro-6-(2-thienyl)benzyloxy]phenyl}-1-cyclohexyl-benzimidazole-5-carboxylicacid,2-{4-[3-chloro-6-(3-chlorophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[3-chloro-6-(3-pyridyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[3-chloro-6-(4-fluorophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-[4-(4-benzyloxyphenoxy)-3-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid,2-[4-(2-bromo-5-chlorobenzyloxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[3-chloro-6-(4-chlorophenyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[2-1(1-acetyl-4-piperidyl)methoxyphenoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[3-{(1-acetyl-4-piperidyl)methoxy}phenoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[3-(2-propynyloxy)phenoxy]phenyl}benzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[3-(3-pyridylmethoxy)phenoxy]phenyl}-benzimidazole-5-carboxylicacid,2-(4-benzyloxy-2-methoxyphenyl)-1-cyclohexylbenzimidazole-5-carboxylicacid,2-[4-(2-bromo-5-methoxybenzyloxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid,2-[4-(carboxydiphenylmethoxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[2-(4-chlorophenyl)-5-nitrobenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[3-acetylamino-6-(4-chlorophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[2-(4-carboxyphenyl)-5-chlorobenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[{(2S)-1-benzyloxycarbonyl-2-pyrrolidinyl}methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{2-chloro-4-[2-(4-trifluoromethylphenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[3-(2-pyridylmethoxy)phenoxy]phenyl}-benzimidazole-5-carboxylicacid,2-{4-[2-(4-chlorophenyl)-5-fluorobenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[3-carboxy-6-(4-chlorophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[3-carbamoyl-6-(4-chlorophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[2-(dimethylcarbamoylmethoxy)phenoxy]phenyl}-benzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[2-(piperidinocarbonylmethoxy)phenoxy]phenyl}-benzimidazole-5-carboxylicacid,2-{4-[{(2S)-1-benzenesulfonyl-2-pyrrolidinyl}methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[{(2S)-1-benzoyl-2-pyrrolidinyl}methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[2-(4-carbamoylphenyl)-5-chlorobenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[3-(dimethylcarbamoylmethoxy)phenoxy]phenyl}-benzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[3-(piperidinocarbonylmethoxy)phenoxy]phenyl}-benzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[3-{(1-methanesulfonyl-4-piperidyl)methoxy}-phenoxy]phenyl}benzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[{2-methyl-5-(4-chlorophenyl)-4-oxazolyl-methoxy]phenyl}benzimidazole-5-carboxylicacid,2-{4-[3-(3-chlorobenzyloxy)phenoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[3-(4-chlorobenzyloxy)phenoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[3-(4-fluorobenzyloxy)phenoxy]phenyl}-benzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[{(2S)-1-(4-nitrophenyl)-2-pyrrolidinyl}-methoxy]phenyl}benzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[{(2S)-1-phenyl-2-pyrrolidinyl}methoxy]phenyl}-benzimidazole-5-carboxylicacid hydrochloride,2-{4-[{(2S)-1-(4-acetylaminophenyl)-2-pyrrolidinyl}methoxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[{5-(4-chlorophenyl)-2-methyl-4-thiazolyl}methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[bis(3-fluorophenyl)methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[2-(4-chlorophenyl)-3-nitrobenzyloxy]phenyl}-benzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[3-(4-tetrahydropyranyloxy)phenoxy]phenyl}-benzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[3-(4-trifluoromethylbenzyloxy)phenoxy]phenyl}-benzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[3-{(1-methyl-4-piperidyl)methoxy}phenoxy]-phenyl}benzimidazole-5-carboxylicacid,2-{4-[3-(4-tert-butylbenzyloxy)phenoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[3-(2-chlorobenzyloxy)phenoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[3-(3-pyridyl)phenoxy]phenyl}benzimidazole-5-carboxylicacid,2-{4-[3-(4-chlorophenyl)phenoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[3-(4-methoxyphenyl)phenoxy]phenyl}-benzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[{4-(4-methanesulfonylphenyl)-2-methyl-5-thiazolyl}methoxy]phenyl}benzimidazole-5-carboxylicacid,2-{4-[{4-(4-chlorophenyl)-2-methyl-5-thiazolyl}methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[1-(4-chlorobenzyl)-3-piperidyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[3-{(2-methyl-4-thiazolyl)methoxy}phenoxy]-phenyl}benzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[3-{(2,4-dimethyl-5-thiazolyl)methoxy}phenoxy]-phenyl}benzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[3-(3,5-dichlorophenyl)phenoxy]phenyl}-benzimidazole-5-carboxylicacid,2-{4-[1-(4-chlorobenzyl)-4-piperidyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[3-(4-chlorobenzyloxy)piperidino]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[4-carbamoyl-2-(4-chlorophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[4-(4-chlorobenzyloxy)piperidino]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[3-{(2-chloro-4-pyridyl)methoxy}phenoxy]pheny}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[{(2S)-1-(4-dimethylcarbamoylphenyl)-2-pyrrolidinyl}-methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[2-(4-chlorophenyl)-5-ethoxycarbonylbenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,1-cyclohexyl-2-[4-(3-trifluoromethylphenoxy)phenyl]-benzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[{4-(4-dimethylcarbamoylphenyl)-2-methyl-5-thiazolyl}methoxy]phenyl}benzimidazole-5-carboxylicacid,2-{4-[2-(4-chlorophenyl)-5-dimethylcarbamoylbenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[{4-(4-chlorophenyl)-2-methyl-5-pyrimidinyl}methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[{2-(4-chlorophenyl)-3-pyridyl}methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride,2-{4-[{3-(4-chlorophenyl)-2-pyridyl}methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[2-(3-chlorophenyl)-4-methylamino-1,3,5-triazin-6-yloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid trifluoroacetate,2-{4-[2-(4-chlorophenyl)-4-(5-tetrazolyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-[4-(4-benzyloxy-6-pyrimidinyloxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[4-(4-pyridylmethoxy)-6-pyrimidinyloxy]phenyl}-benzimidazole-5-carboxylicacid,2-{4-[4-(3-chlorophenyl)-6-pyrimidinyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid, methyl2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylate,2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride, ethyl2-{4-[3-(4-chlorophenyl)pyridin-2-ylmethoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylate,methyl2-[4-(2-bromo-5-tert-butoxycarbonylbenzyloxy)phenyl]-1-cyclohexylbenzimidazole-5-carboxylate,methyl2-{4-[5-tert-butoxycarbonyl-2-(4-chlorophenyl)benzyloxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylate,methyl2-{4-[5-carboxy-2-(4-chlorophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylatehydrochloride, methyl2-{4-[2-(4-chlorophenyl)-5-methylcarbamoylbenzyloxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylate,2-{4-[2-(4-chlorophenyl)-5-methylcarbamoylbenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[3-(tert-butylsulfamoyl)-6-(4-chlorophenyl)benzyloxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[2-(4-chlorophenyl)-5-sulfamoylbenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid trifluoroacetate,2-(4-benzyloxycyclohexyl)-1-cyclohexylbenzimidazole-5-carboxylic acidhydrochloride,2-[2-(2-biphenylyloxymethyl)-5-thienyl]-1-cyclohexylbenzimidazole-5-carboxylicacid,2-[2-(2-biphenylyloxymethyl)-5-furyl]-1-cyclohexylbenzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[{4-(4-fluorophenyl)-2-hydroxymethyl-5-thiazolyl}methoxy]phenyl}benzimidazole-5-carboxylicacid,1-cyclohexyl-2-{4-[{4-(4-carboxyphenyl)-2-methyl-5-thiazolyl}-methoxy]phenyl}benzimidazole-5-carboxylicacid hydrochloride,1-cyclohexyl-2-{2-fluoro-4-[4-fluoro-2-(3-fluorobenzoyl)-benzyloxy]phenyl}benzimidazole-5-carboxylicacid,2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-sulfonicacid,2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-3-cyclohexylbenzimidazole-4-carboxylicacid,1-cyclohexyl-2-{4-[3-dimethylcarbamoyl-5-(4-pyridylmethoxy)-phenoxy]phenyl}benzimidazole-5-carboxylicacid dihydrochloride,1-cyclohexyl-2-{4-[3-carboxy-5-(4-pyridylmethoxy)phenoxy]-phenyl}benzimidazole-5-carboxylicacid dihydrochloride,2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-1-cyclohexylbenzimidazole-4-carboxylicacid,2-{4-[3-carbamoyl-6-(4-chlorophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[{2-(4-carboxyphenyl)-3-pyridyl}methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-1-(4-tetrahydrothiopyranyl)benzimidazole-5-carboxylicacid,2-{4-[2-(4-chlorophenyl)-5-dimethylcarbamoylbenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,1-cyclohexyl-2-{4-[3-dimethylcarbamoyl-6-(4-trifluoromethylphenyl)benzyloxy]phenyl}benzimidazole-5-carboxylicacid hydrochloride,1-cyclohexyl-2-{4-[3-dimethylcarbamoyl-6-(4-methylthiophenyl)-benzyloxy]phenyl}benzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-methylcarbamoylbenzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-dimethylcarbamoylbenzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[3-carbamoyl-6-(4-chlorophenyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[3-dimethylcarbamoyl-6-(4-methanesulfonylphenyl)-benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[3-dimethylcarbamoyl-6-(3-pyridyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride,2-{4-[3-dimethylcarbamoyl-6-(4-dimethylcarbamoylphenyl)-benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]-2-fluorophenyl}-1-(4-tetrahydrothiopyranyl)benzimidazole-5-carboxylicacid,2-{4-[2-(4-chlorophenyl)-5-dimethylsulfamoylbenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-methanesulfonylbenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride, methyl2-{4-[5-carboxy-2-(4-chlorophenyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylatehydrochloride,2-{4-[2-(4-chlorophenyl)-5-dimethylaminobenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride,2-{4-[2-(4-chlorophenyl)-5-methanesulfonylaminobenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-diethylcarbamoylbenzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-isopropylcarbamoylbenzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-piperidinocarbonylbenzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(1-pyrrolidinyl)carbonylbenzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(2-hydroxyethyl)carbamoylbenyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(4-hydroxypiperidino)-carbonylbenzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-morpholinocarbonylbenzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-thiomorpholinocarbonylbenzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[3-(carboxymethylcarbamoyl)-6-(4-chlorophenyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-{4-(2-carboxyethyl)phenyl}-5-chlorobenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[3-chloro-6-(4-hydroxymethylphenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[3-chloro-6-(4-methoxymethylphenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(3-carboxyphenyl)-5-chlorobenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[2-(4-chlorophenyl)-5-methylthiobenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[2-(4-chlorophenyl)-5-methylsulfinylbenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[2-(4-chlorophenyl)-5-cyanobenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[bis(3-pyridyl)methoxy]-2-fluorophenyl-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[bis(4-dimethylcarbamoylphenyl)methoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid, sodium2-{4-[2-thienyl-3-thienylmethoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylate,methyl2-{4-[2-(4-chlorophenyl)-5-(dimethylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylate,sodium2-{4-[2-(4-chlorophenyl)-5-(dimethylcarbamoyl)benazyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylate,2-{4-[5-carboxy-2-(4-chlorophenyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[2-(4-carboxyphenyl)-5-methoxybenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[2-(4-carbamoylphenyl)-5-(dimethylcarbamoyl)benzyloxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[5-amino-2-(4-chlorophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[5-(4-chlorophenyl)-2-methoxybenzylsulfinyl]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[5-(4-chlorophenyl)-2-methoxybenzylsulfonyl]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-methoxybenzylthio]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[bis(4-carboxyphenyl)methoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-[4-(phenyl-3-pyridylmethoxy)-2-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid, methyl2-{4-[2-(4-chlorophenyl)-5-(methylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylate,2-{4-[5-chloro-2-(4-pyridyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(benzylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(cyclohexylmethylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(4-pyridylmethylcarbamoyl)tbenzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride,2-{4-[2-(4-chlorophenyl)-5-(N-benzyl-N-methylcarbamoyl)-benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride, methyl2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-1-cyclohexyl-1H-indole-5-carboxylate,2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-1-cyclohexyl-1H-indole-5-carboxylicacid, 2-(4-benzyloxyphenyl)-1-cyclopentyl-1H-indole-5-carboxylic acid,ethyl2-(4-benzyloxyphenyl)-3-cyclohexylimidazo[1,2-a]pyridine-7-carboxylate,2-(4-benzyloxyphenyl)-3-cyclohexylimidazo[1,2-a]pyridine-7-carboxylicacid, and2-{4-[2-(4-chlorophenyl)-5-methoxybenzyloxy]phenyl}-3-cyclohexyl-3H-imidazo[4,5-b]pyridine-6-carboxylicacid.
 92. The fused ring compound of claim 42 or a pharmaceuticallyacceptable salt thereof, which is selected from the group consisting of2-{4-[5-dimethylaminocarbonyl-2-(4-pyridyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride,2-{4-[2-(4-chlorophenyl)-5-(4-methylpiperazin-1-ylcarbonyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride,2-{4-[2-(4-chlorophenyl)-5-{N-(3-pyridylmethyl)carbamoyl}-benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride,2-{4-[2-(4-chlorophenyl)-5-{N-(2-pyridylmethyl)carbamoyl}-benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride,2-{4-[2-(4-chlorophenyl)-5-(cyclohexylcarbamoyl)benzyloxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(2-pyridin-4-ylethylcarbamoyl)-benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride,2-{4-[(4-fluorophenyl){4-(dimethylaminocarbonyl)phenyl}methoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[(4-fluorophenyl)(4-carboxyphenyl)methoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[2-(4-chlorophenyl)-5-(4-oxopiperidinocarbonyl)benzyloxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-hydroxybenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(isopropylcarbamoyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(N-isopropyl-N-methylcarbamoyl)-benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(phenylcarbamoyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(4-methoxypiperidinocarbonyl)-benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(3-hydroxypropyloxy)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid, and2-{4-[2-(4-chlorophenyl)-5-(2-hydroxyethoxy)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride.
 93. The fused ring compound of claim 42 or apharmaceutically acceptable salt thereof, which is selected from thegroup consisting of methyl2-[4-(2-bromo-5-nitrobenzyloxy)-2-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylate,methyl2-[4-{2-(4-chlorophenyl)-5-nitrobenzyloxy}-2-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylate,methyl2-[4-{5-amino-2-(4-chlorophenyl)benzyloxy}-2-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylate,methyl2-[4-{2-(4-chlorophenyl)-5-(2-oxopyrrolidin-1-yl)benzyloxy}-2-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylate,2-[4-{2-(4-chlorophenyl)-5-(2-oxopyrrolidin-1-yl)benzyloxy}-2-fluorophenyl]-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(4-methylpiperidin-1-ylcarbonyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[5-acetyl-2-(4-chlorophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-1(4-hydroxypiperidin-1-ylcarbonyl)methoxybenzyloxylphenyl}-1-cyclohexylbenzimidazole-5-carboxylic acid,2-{4-[2-(4-chlorophenyl)-5-(2-methoxyethoxy)benzyloxy]pphenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-{2-(2-methoxyethoxy)ethoxy}benzyloxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[{2-(4-chlorophenyl)-5-(isobutylcarbonyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[2-(4-chlorophenyl)-5-(2-methylthiazol-4-yl)benzyloxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[2-(4-chlorophenyl)-5-(3,4-dihydroxypiperidin-1-ylcarbonyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(3-methyl-1,2,4-oxadiazol-5-yl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-4-(isopropylcarbamoyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-4-(piperidinocarbonyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-{(1-hydroxy-2-methylpropan-2-yl)carbamoyl}benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(4,4-dimethyl-2-oxazolin-2-yl)}benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride,2-{4-[2-(4-chlorophenyl)-4-(4-hydroxypiperidin-1-ylcarbonyl)-benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-4-{(2-hydroxyethyl)carbamoyl}benzyloxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-4-{(4-pyridylmethyl)carbamoyl}-benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[2-(4-chlorophenyl)-4-(dimethylcarbamoyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[5-(2-aminothiazol-4-yl)-2-(4-chlorophenyl)benzyloyy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride,2-{4-[2-(4-chlorophenyl)-5-(4-hydroxypiperidin-1-ylsulfonyl)-benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[5-(dimethylcarbamoyl)-2-(4-fluorophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[5-(dimethylcarbamoyl)-2-(3-fluorophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(5-chlorothiophen-2-yl)-5-(dimethylcarbamoyl)benzyloxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-bromo-5-(5-methyloxazol-2-yl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-bromo-5-(5-methylthiazol-2-yl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(5-methyloxazol-2-yl)benzyloxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(5-methylthiazol-2-yl)benzyloxy]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-tetrazol-5-ylbenzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[5-chloro-2-(4-cyanophenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[5-chloro-2-(4-tetrazol-5-ylphenyl)benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-{2-(4-hydroxypiperidin-1-yl)ethoxy}benzyloxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(2-oxopiperidin-1-yl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[3-(4-chlorophenyl)-5-(dimethylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(N-hydroxyamidino)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride,2-{4-(2-(4-chlorophenyl)-5-(2,5-dihydro-5-oxo-4H-1,2,4-oxadiazol-3-yl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(2-oxo-3H-1,2,3,5-oxathiadiazol-4-yl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(2,5-dihydro-5-oxo-4H-1,2,4-thiadiazol-3-yl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(cyclopropylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(cyclobutylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(tert-butylcarbamoyl)benzylcixy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(isobutylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-{(1-hydroxypropan-2-yl)carbamoyl}-benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(methoxycarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-{(2,3-dihydroxypropyl)carbamoyl}-benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(N-ethyl-N-methylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(N-methyl-N-propylcarbamoyl)-benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(N-isopropyl-N-methylcarbamoyl)-benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(2,6-dimethylpiperidin-1-ylcarbonyl)-benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[5-(butylcarbamoyl)-2-(4-chlorophenyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(propylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(ethylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-{(dimethylcarbamoyl)amino}benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-{(morpholinocarbonyl)amino}benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-ureidobenzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-{(ethylcarbamoyl)amino}benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-{(isopropylcarbamoyl)amino}benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(3,4-difluorophenyl)-5-(isopropylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[2-(2,4-difluorophenyl)-5-(isopropylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(3,5-dichlorophenyl)-5-(isopropylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(3-chloro-4-fluorophenyl)-5-(isopropylcarbamoyl)-benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(3,4-dichlorophenyl)-5-(isopropylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chloro-2-fluorophenyl)-5-(isopropylcarbamoyl)-benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chloro-2-fluorophenyl)-5-(pyrrolidin-1-ylcarbonyl)-benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chloro-3-fluorophenyl)-5-(pyrrolidin-1-ylcarbonyl)-benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chloro-3-fluorophenyl)-5-(isopropylcarbamoyl)-benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-{4-(methylthio)phenyl}-5-(2-oxopyrrolidin-1-yl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-{4-(methylthio)phenyl}-5-(isopropylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[4-chloro-2-(4-chlorophenyl)-5-(1,1-dioxoisothiazolidin-2-yl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[4-chloro-2-(4-chlorophenyl)-5-(2-oxopyrrolidin-1-yl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(isopropylaminosulfonyl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(dimethylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclopentylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(4-hydroxypiperidin-1-ylcarbonyl-benzyloxy]-2-fluorophenyl}-1-cyclopentylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(isopropylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclopentylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(isopropylcarbamoyl)benzyloxy]phenyl}-1-cyclopentylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(dimethylcarbamoyl)benzyloxy]phenyl}-1-cyclopentylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(4-hydroxypiperidin-1-ylcarbonyl)-benzyloxy]phenyl}-1-cyclopentylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(isopropylcarbamoyl)benzyloxy]phenyl}-1-(tetrahydrothiopyran-4-yl)benzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(pyrrolidin-1-ylcarbonyl)benzyloxy]-phenyl}-1-(tetrahydrothiopyran-4-yl)benzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(isopropylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-(tetrahydrothiopyran-4-yl)benzimidazole-5-1-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(2-oxopyrrolidin-1-yl)benzyloxy]-2-fluorophenyl}-1-(tetrahydrothiopyran-4-yl)benzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(isopropylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-piperidinobenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(pyrrolidin-1-ylcarbonyl)benzyloxy]-2-fluorophenyl}-1-piperidinobenzimidazole-5-carboxylicacid,2-{4-[2-(4-chlorophenyl)-5-(2-imidazolin-2-yl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride,2-{4-[2-(4-chlorophenyl)-5-(2-oxooxazolidin-3-yl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(2-oxoimidazolidin-1-yl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(2-oxazolin-2-ylamino)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride,2-{4-[{2-[{(dimethylcarbamoyl)methoxy}methyl]-4-(4-fluorophenyl)thiazol-5-yl}methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[{4-(4-fluorophenyl)-2-(4-hydroxypiperidin-1-ylmethyl)thiazol-5-yl}methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid dihydrochloride,2-{4-[{4-(4-fluorophenyl)-2-[(carbamoylmethoxy)methyl]thiazol-5-yl}methoxy]phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[{4-(4-fluorophenyl)-2-(methylcarbamoyl)thiazol-5-yl}methoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[{4-(4-fluorophenyl)-2-1(2-hydroxyethyl)carbamoyl}thiazol-5-yl}methoxy]-2-fluorophenyl-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[{2-(4-fluorophenyl)-5-(dimethylcarbamoyl)thiophen-3-yl}methoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[{2-(4-fluorophenyl)-5-(isopropylcarbamoyl)thiophen-3-yl}methoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride, 2-{4-[{2-(4-fluorophenyl)-5-(4-hydroxypiperidin-1-ylcarbonyl)thiophen-3-yl}methoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(dimethylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexyl-5-tetrazol-5-ylbenzimidazole,2-{4-[2-(4-carboxyphenyl)-5-chlorobenzyloxy]-2-fluorophenyl}-1-cyclohexyl-5-tetrazol-5-ylbenzimidazolehydrochloride,2-{4-[2-(4-chlorophenyl)-5-(isopropylcarbamoyl)benzyloxy]-2-fluorophenyl}-1-cyclohexyl-5-(2,5-dihydro-5-oxo-4H-1,2,4-oxadiazol-3-yl)benzimidazolehydrochloride,2-{4-[5-carboxy-2-(4-chlorophenyl)benzyloxy]-2-fluorophenyl}-5-cyano-1-cyclohexylbenzimidazole,2-{4-[2-(4-chlorophenyl)-5-(dimethylcarbamoyl)benzyloxy]-2-fluorophenyl}-5-cyano-1-cyclohexylbenzimidazole,2-{4-[{N-(4-dimethylcarbamoyl)-N-(4-fluorophenyl)amino}methyl]-phenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{5-[bis(3-fluorophenyl)methyl]-2-fluoro-4-hydroxyphenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{3-[bis(3-fluorophenyl)methyl]-2-fluoro-4-hydroxyphenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid,2-{4-[(3-dimethylcarbamoylphenyl)(4-fluorophenyl)methoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[{3-(4-hydroxypiperidyl-1-ylcarbonyl)phenyl}(4-fluorophenyl)methoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,1-{[2-{4-([4-(4-fluorophenyl)-2-methylthiazol-5-yl]methoxy)phenyl}-1-cyclohexylbenzimidazol-5-yl]carbonyl}-β-D-glucuronicacid,{[2-{4-[bis(3-fluorophenyl)methoxy]-2-fluorophenyl}-1-cyclohexylbenzimidazol-5-yl]carbonyl}-β-D-glucuronicacid,2-{4-[2-(4-chlorophenyl)-5-(1,1-dioxoisothiazolidin-2-yl)benzyloxy]-2-fluorophenyl}-1-cyclohexylbenzimidazole-5-carboxylicacid hydrochloride,2-{4-[2-(4-chlorophenyl)-5-(isopropylcarbamoyl)benzyloxy]phenyl}-3-cyclohexyl-3H-dimidazo[4,5-b]pyridine-6-carboxylicacid hydrochloride, and2-{4-[2-(4-chlorophenyl)-5-(pyrrolidin-1-ylcarbonyl)benzyloxy]-phenyl}-3-cyclohexyl-3H-imidazo[4,5-b]pyridine-6-carboxylicacid hydrochloride.
 94. A pharmaceutical composition comprising a fusedring compound of claim 42, or a pharmaceutically acceptable saltthereof, and a pharmaceutically acceptable carrier.
 95. A hepatitis Cvirus polymerase inhibitor comprising a fused ring compound of claim 1,or a pharmaceutically acceptable salt thereof, and a pharmaceuticallyacceptable carrier.
 96. An anti-hepatitis C virus agent comprising afused ring compound of claim 1, or a pharmaceutically acceptable saltthereof, and a pharmaceutically acceptable carrier.
 97. A therapeuticagent for hepatitis C comprising a fused ring compound of claim 42, or apharmaceutically acceptable salt thereof, and a pharmaceuticallyacceptable carrier.
 98. An anti-hepatitis C virus agent comprising (a)the anti-hepatitis C virus agent of claim 96 and (b) at least one agentselected from the group consisting of a different antiviral agent, anantiinflammatory agent and an immunostimulant.
 99. An anti-hepatitis Cvirus agent comprising (a) the anti-hepatitis C virus agent of claim 96and (b) interferon.
 100. A therapeutic agent for hepatitis C comprising(a) the hepatitis C virus polymerase inhibitor of claim 95 and (b) atleast one agent selected from the group consisting of a differentantiviral agent, an antiinflammatory agent and an immunostimulant. 101.A therapeutic agent for hepatitis C comprising (a) the hepatitis C viruspolymerase inhibitor of claim 95 and (b) interferon.
 102. Abenzimidazole compound of the following formula [III]

wherein R^(a36) is hydrogen atom or carboxyl-protecting group, R^(a37)is cyclopentyl or cyclohexyl, and R^(a38) is hydrogen atom or fluorineatom, or a salt thereof.
 103. A thiazole compound selected from thegroup consisting of 4-(4-fluorophenyl)-5-hydroxymethyl-2-methylthiazoleand 4-(4-fluorophenyl)-5-chloromethyl-2-methylthiazole, or apharmaceutically acceptable salt thereof.
 104. A pharmaceuticalcomposition comprising (a) the fused compound of the formula [I] ofclaim 1 or a pharmaceutically acceptable salt thereof and (b) at leastone agent selected from the group consisting of an antiviral agent otherthan the compound of claim 1, an antiinflammatory agent and animmunostimulant.
 105. A pharmaceutical composition comprising (a) thefused compound of the formula [I] of claim 1 or a pharmaceuticallyacceptable salt thereof and (b) interferon.
 106. A method for treatinghepatitis C, which comprises administering an effective amount of afused ring compound of the formula [I] of claim 1 or a pharmaceuticallyacceptable salt thereof.
 107. The method of claim 106, furthercomprising administering an effective amount of at least one agentselected from the group consisting of an antiviral agent other than thecompound of claim 1, an antiinflammatory agent and an immunostimulant.108. The method of claim 106, further comprising administering aneffective amount of interferon.
 109. A method for inhibiting hepatitis Cvirus polymerase, which comprises administering an effective amount of afused ring compound of the formula [I] of claim 1 or a pharmaceuticallyacceptable salt thereof.
 110. The method of claim 109, furthercomprising administering an effective amount of at least one agentselected from the group consisting of an antiviral agent other than thecompound of claim 1, an antiinflammatory agent and an immunostimulant.111. The method of claim 109, further comprising administering aneffective amount of interferon.